Anxiety
by Cupzy
Summary: The first fanfic I have ever written. Inspired by Redoktober When a young man named Jack gets stuck in Equestria, he develops a relationship with Rainbow Dash. Rated T because of my dirty dirty language
1. Meet Jack

Anxiety

Jack was always a smart boy, he remained calm no wonder what kind of situation he found himself in, he was slightly muscular, he wasn't a bodybuilder he just looked... natural. But a couple of weeks ago Jack went to sleep per usual and woke up feeling normal as ever, he got himself a bowl of cornflakes and afterwards got ready for school, he packed his bag and stepped outside, but instead of being greeted by a pollution-filled and crowded part of London, he was in the middle of a forest. Naturally, he started panicking but shortly regained his composure and told himself to remain calm, he stepped out into the forest and surveyed his surroundings. Everything looked natural, the waving of the trees, the sounds of birds chirping, it was actually pretty relaxing. But nonetheless he had to find a way out. With or without his house

Meanwhile, in the well-known town of Ponyville, a violet pony named Twilight sparkle was just waking up, she had bags under her eyes due to the incredible amount of studying she did last night on Equestria's history. "Spiiiiiiiiike!" she called just as a small purple baby dinosaur rose from his bed and immediately heard Twilight's pleas _"What could she possibly want this early in the morning?" _Spike thought to himself as he tried to rub the sleep from his eyes. Twilight was standing looking at the bookcase entitled _"Equestrian history"_ where Spike knew he was going to have another day looking through dusty old books for information about the elements of harmony, as Twilight was still intrigued by the way they worked.

"Ah, there you are Spike, what took you so long to get here?" Twilight exclaimed while looking through the shelves. "Uh, I was kinda sleeping, maybe you should go take a nap or something, you went to bed pretty late last night" Spike wasn't lying, Twilight's mane was frazzled at some points and she was having a hard time keeping her eyes open. "Oh, Spike, there's no need for THAT much sleep when you have studying to do!" Twilight exclaimed as her horn glowed dark purple and a book levitated to the ground. "Here we go, I've found the book I was looking for!" Twilight wanted to know more about the elements of harmony because she never had a humongous understanding of how they worked, or how much magical power they actually had.

Back at Jack's house, he was still trying to put two and two together and figure out how the hell he ended up in a forest. His first guess was that he got pretty drunk last night and ended up in the forest, but he didn't think he could carry his house all the way out here. He didn't recognize the forest because he didn't actually live near any. He went back into the house and tried to settle down, after all, he was gonna be here for a while. Out of his window, he managed to spot some sort of creature, he couldn't tell what it actually was but he noticed that it was on four legs and was pale-yellow. He stepped outside and came up on the creature from behind, he realized it must have been a pony. But... ponies don't come in yellow, right? "Um... hi" Jack said to the pony, obviously as a joke, because animals can't talk english. The pony suddenly jumped and spun around. Jack noticed the pony had something next to it's right leg, near the rump but he couldn't point it out in the short time allotted. The pony was very well groomed, it had pink hair that went down the right side of it's face. "Um... hi" Jack's jaw dropped, a pony just talked to him, it was quiet but he heard it, he pinched himself to make sure that this wasn't a dream, it wasn't.

"Did... you just... talk?" Jack said in disbelief, "Uh... yeah?" whatever it was, this thing was shy and it didn't seem to enjoy conversation. "what are you?" said jack, still amazed by the phenomenon. "Uh... I'm a pegasi, what are you?" _"What am I?! she's a fucking talking pony!" _and that's when Jack realized, the pony had two wings sprouting from it's back, this was a Pegasus Jack had a lot of interest in mythology and already knew what a Pegasus was. "Do you... have a name?" The Pegasus stayed silent for a moment and then spoke "Um... my name's Fluttershy... what's yours?" _"Fluttershy, huh? well, it's appropriate, to say the least" _Jack thought, and then he spoke up "My name's Jack, could you please tell me where I am?" "Well... you're in the everfree forest, I was taking a stroll through and I heard something something and I thought it was an animal so I went to go investigate. I work as an animal keeper in Ponyville..." Fluttershy said. _"Wait, what? she WORKS?! Ponyville? what's she talking about?" _Jack thought.

"Where's ponyville? and why do you work? You're a PONY!" Jack exclaimed. The outburst startled Fluttershy and she ran for it. "Wait, I have so many questions!" Jack said as he began to give chase. The pony was fast, for sure, but Jack managed to keep a pace and eventually Fluttershy ran back to some sort of town. Jack took cover behind a bush, he didn't want anyone to see him chasing a yellow and shy Pegasus. He lost track of Fluttershy but at least he found civilization. He walked into the village realizing that everyone in the village seemed to live in tree houses. What Jack was REALLY concerned about, however, was that the residents were PONIES. He got some strange looks from the residents in the town, given that he was human. He eventually found an extremely large treehouse and thought that he might ask for information there. He knocked on the door and was greeted by Twilight Sparkle. "Um... hello." Jack said and the pony gave him a very odd look "Ummm... what are you? You speak English so clearly you're sentient, but you don't look like a pony..." Twilight said _"Pardon me? I look SENTIENT? I should be the one telling her that." _Jack thought to himself. "Would you like to come inside?" Said twilight sparkle with an interested smile. "Yeah, ok, sure" Mike replied as he walked inside the building, he immediately realized that the house was in fact a library with countless books. "Do you live here?" said Jack with a hint of interest "Yes I do, I've read every book in this library at least twice" Said Twilight. "Um... ok" replied Jack, confused.

"Well, back to the matter at hand, who are you, or more importantly WHAT are you?" Twilight said curiously. "Excuse me? I believe I should be asking YOU that question" Jack said with a slight chuckle. "I'm Twilight Sparkle, I am the student of princess Celestia, the leader of Equestria." Twilight said triumphantly. "This may just be crazy talk but I believe I'm from another world where ponies CAN'T talk and I have no clue what you're talking about" Jack said. Twilight then begins briefly informing Jack of Equestria's history. And how ponies are the sole rulers of it. "Well, ok, I'm a human, do you have any of those in Equestria?" Said Jack. "No. but you came from a different world so that doesn't seem much of a surprise." said Twilight. "Ok, I see, I should probably head back to my house, I need to think this over a little, I'll see you tomorrow, Twilight Sparkle." Jack said. "Just call me Twilight" she exclaimed.

Mike started walking back to his house trying to grasp the situation he was in _"Ok, I'm somehow in a world where ponies rule, I wont question that at this point in time but I have to get my bearings and try to live it out until I find a way to go back to my world. You never know, living in Ponyville might not be so bad..."_

Jack pulled out a Journal and started to write in it, he always carries it around with him to dossier things.

_Dear diar- oh fuck that was pen. Um... entry 1 I suppose_

_If anyone (human preferably) finds this, this is a dossier about my experiences in Ponyville, stupid name for a town right? Wrong. the residents of Ponyville are ACTUALLY PONIES. THAT CAN WALK. AND TALK. AND USE MAGIC! creepy, right? anyway, seems like I'm stuck here until I find some way to get out, my house came with me so at least I have somewhere to stay. I met these two ponies today. One was called Fluttershy, fitting name considering she ran away as soon as I raised my voice. And this less-shy one called Twilight Sparkle. She wants me to go to her house/library (I know, right?) and give me more information on Equestria (the country,__ basically) hopefully I'll be able to get back soon_

_-Jack Tailor_

**Well, that was the first chapter of my first fanfic Anxiety, I hope you liked it. Credit goes to RedOktober for A) turning me into a brony and B) inspiring me to write this. I'll probably update frequently because I don't go to school yet (Because I just moved from Scotland to England and finding a school had been a Beeyotch.  
**


	2. The land of Equestria

Jack woke up feeling normal, he went downstairs in his usual mood and made himself some beans on toast and sat down, using the TV remote to flick to a random channel. Wait, no reception? he took a look outside and remembered "Oh yeah... Shit, I'm still here aren't I?" Jack remembered that he was still in the land of Equestria, he guessed they didn't have TV's here and wondered what he would do for the rest of the day. He was going to go to Twilight's house at around 1 o clock so he had to find some sort of activity to pass the time, suddenly, he heard a rustling outside. He went to looked out the window moments before being knocked to the ground by a large cyan object. Jack was in considerable pain, his nose seemed to be bleeding and he had a hard time getting up. "Hey! are you okay? sorry for hitting you." Jack mustered the strength to lift himself up and noticed a pony standing in front of him, the pony had bright cyan fur and it's mane was colored like a rainbow. "Twilight told me there was a talking creature living in the woods but I never believed her!" The cyan pony exclaimed. "Well, I'm really not in the mood right now for visitors considering my TV doesn't work" John told the pony. "Huh? a "TV" what's that?" The pony said _"Yeah, they don't have TV's here, I hit that nail right on the head" _Jack thought. "Hey, you don't talk much, you remind me of Fluttershy" the pony said with a giggle. it was hard to tell if the pony was a boy or a girl, but the rainbow colors and the voice gave it away, she was female. Her voice was odd, the pony seemed quite young but her voice was strained at some points, like an old woman trying to raise her voice. "So, now that you barged into my house you wanna tell me who you are?" John said angrily, dabbing his nose with the back of his hand and pulling it away. Yep, blood. "My name's Rainbow Dash, the fastest pony in all of Equestria!" she said with a victorious pose to match her personality.

Jack could already tell Rainbow Dash was egomanaical, she took every opportunity to gloat and she seemed very tomboyish. "Alright, so why did you break into my house and assault me?" Jack asked sarcastically. "Oh. Twilight sent me, I'm one of her best friends. She told me to come here so I could remind you about coming over to her house to talk about stuff" Rainbow Dash said "Ah, I see. Well tell her there's nothing to worry about, I knew about it, I was gonna come down around one-ish." Jack explained. "Oh, Ok. I'll go tell her that!" Said Rainbow Dash as she spread her wings but she was interrupted my Jack. "Hey, you said I remind you a lot of Fluttershy, do you know her?" Jack asked. "Oh yeah, she's really shy, and she doesn't bode well with strangers." Rainbow said.

"Well, if you see her tell her I'm sorry for scaring her away." Jack said, half expecting Rainbow Dash to take it the wrong way and hurt him even more. "Wait, have you met her?" Rainbow Dash exclaimed. "Yeah, she bolted as soon as I asked what she worked as..." Jack said, half lying seeing as he raised his voice at her instead. Rainbow Dash nodded and spread her wings, before Jack could react she blasted through another one of Jack's windows. _"Hmm, something tells me I'm not going to get along with her" _Jack thought to himself. _"I don't have anything else to do today so I might as well visit Twilight." _

Jack took his schoolbag and packed it with a packet of crisps (That's chips in america) and a water bottle. Seeing as it would be indecent to go there in his PJ's, he put on a plain white shirt and blue jeans. Since that was his only pair of clean clothes and his washing machine probably wasn't going to work anytime soon, unless the ponies had electricity. He flung the rucksack over his shoulder and left the house. Due to the urgency of last time, he never actually got to take a good look at the forest, it looked like any other forest, the trees were large and the forest had a creepy atmosphere around it, did Equestria have different creatures to the human world, were they docile or much more aggressive than earth's creatures?

Either way Jack decided he wouldn't spend a lot of time in the forest during midnight. He eventually found an opening in the forest from going the same way he went last time, and sure enough the village was in sight over the horizon. Jack kept a low profile as soon as he entered the village although his curiosity got the better of him and he started to investigate Ponyville further. It was only 11 o clock so he had plenty time before he had to go to Twilight's house. As he was exploring the town, a pony ran head first into his leg, sweeping him off balance and almost knocking him over.

He regained his composure and walked over to the pony that was knocked onto it's side. "Um... do you need a hand?" Said Jack as he helped the pony get back up. The pony was a bright pink and it's mane was... also pink. "Hey! you don't look like a pony!" The pony said loudly with genuine excitement in it's voice. "That's probably because I'm not. My name's Jack, I'm a human." Jack explained. "Oh! Twilight said something about a hu- a hoo- a- A HUMAN! yeah! she said there was something like that living in the forest!" The pony said acting extremely happy. "I suppose you're one of her friends, then?" Jack asked, still dumbfounded by the amount of energy the pony had. "Oh yeah! My name's Pinkie Pie! I LOOOOOOOVE throwing parties!" Pinkie Pie said, her voice getting louder. "Nice to meet you Pinkie." Jack said as he held out a hand. "Um... why do you have worms growing out of the ends of your hoof?" Pinkie Pie asked as she inspected Jack's hand. "Um... it's called a finger, we use it to pick stuff up." Jack explained. "But we can pick stuff up already!" said Pinkie as she picked up a stone to prove it.

She wasn't using any fingers or "magic" but she still managed to hold the stone in her hand. "Well, anyway I was just taking a tour around the town until I go to Twilight Sparkle's house." Jack told Pinkie. "Oh, ok. I'll see you later then!" Said Pinkie as she ran away from Jack, giving a wave. Jack continued his tour around town until he came to what looked like some kind of fashion parlor. He knocked on the door. _"Maybe they have someone in here who could wash my laundry?" _Jack thought. The door opened, revealing a white pony with a purple mane, she looked more well groomed than the other ponies. Her mane was curled along with her tail. "Oh, hello there! You must be the... what was it again? Human? Oh well, I've forgotten. Please come inside!" Said the pony. She had a British accent, the same as Jack which he found quite intriguing. "Hello, my name's Jack. I came here to visit Twilight Sparkle but I was taking a tour around Ponyville first." Jack said.

"I was wondering if you did a laundry service here?" Jack asked. "Oh yes, darling. I have the best fashion sense in all of Equestria! Of course I would help you!" Said The white pony. "My name's Rarity." "Thanks for the help, Rarity" Said Jack. "No problem, darling. If you bring your washing next time you come around then you can just leave it with me!" Said Rarity as Jack left the Parlor. _"Ok, I'd better start heading to Twilight's If I want to make it there on time" _Jack though to himself. _"Ummm... I'm pretty sure it was this way..." _Jack said as he started walking.

After asking for directions a few times, Jack managed to reach Twilight's house with five minutes to spare. He knocked on the door expecting Twilight to answer, But instead a small purple creature answered the door. "Ah, hello you must be Jack, right?" The small creature explained. But Jack was still trying to figure out what the creature actually was... "Um... hello, my name's Jack... What exactly are you? If you don't mind me asking?" Jack pondered. "Me? I'm a baby dragon! My name's Spike!" Said Spike. _"Oh wow, so Ponies aren't the only sentient creatures here on Equestria. Dragons too?" _Jack thought to himself, he then realized that the creature did in fact resemble a dragon from mythology. "Do you wanna come in?" Spike asked. "Oh, yeah." Jack said, recovering his thought process.

He stepped inside to the familiar library that he saw yesterday, everything looked exactly the way it was last time. The library was clearly well looked after. "Twilight! Jack's here to see you!" Spike shouted out. Jack saw Twilight come out from the back of one of the bookcases. "Ah, Jack. I was wondering when you were coming. Rainbow Dash told me that you were coming around 1 o clock but I never expected you to be so precise!" said Twilight with a giggle. Jack looked at his watch, the clock hands pointed to exactly one o clock. He timed it perfectly. "It's nice to see you too Twilight." Jack said. "Do you want a cup of tea or coffee?" asked Twilight. "Nah, it's alright, I brought some stuff to eat" Said Jack. _"Wow, they actually drink tea and coffee here? Maybe they aren't so different from humans after all..." _Jack thought.

"Well, I invited you over to teach you more about Equestria and give you a rundown of our culture." Twilight explained as she sat down and pulled up a chair for Jack to sit on. "Alright." Jack said as he sat down. Twilight then proceeded to give him a brief rundown of all of Equestria's culture. "So we have two princesses-" Twilight said as she was cut off by Jack. "Wait, wait, wait. TWO princesses?" Exclaimed Jack "Where's the king?!" He asked. "We don't have a king, we have princess Celestia and princess Luna. Celestia's in charge of raising the sun every morning and Luna's in charge of raising the moon every night. "Oh wow, that's a big change." Said Jack. "What do you mean?" asked Twilight. "Well in our world the sun and the moon raise by themselves, gravity and stuff. and the government changes depending on the country." Jack explained. "Oh, well we only have two princesses" Twilight answered.

"Didn't you say that you were the student of someone named Celestia?" Asked Jack. "Oh, yeah! I'm the student of princess Celestia!" Twilight said triumphantly. "Oh, so are you, like the future princess or something?" Jack joked. Twilight blushed a little. "No, it's just that I have a lot of magical power and the princess wants me to harness the power of friendship to control my magical powers." Twilight explained. "I see..." Said Jack. The duo talked through the night, teaching each other of their various cultures and systems. By the end Jack knew everything basic about equestria, cutie marks and stuff like that. "Well, you must be tired. We have a spare room upstairs if you want to sleep there." Twilight offered. "Thanks. I'll probably go upstairs and get ready for bed then." Jack said. He walked upstairs and into the bedroom. The bed looked comfy enough and the room was in good shape. He put on his PJ's and jumped into the bed. He took out his Dossier and started to write in it.

_Dear Diar- Oh crap I did it again! Ok, entry 2_

_I took a tour around Ponyville today, I met a couple of Twilight's friends while I was doing that. I met this pink one called Pinkie Pie, she was REALLY energetic and she said she loved throwing parties. There was a cyan one called Rainbow Dash, she was arrogant as all hell but she was pretty cool __nonetheless, There was a white one with a purple mane called Rarity, she had an English accent so at least I had something to relate to In Ponyville. Twilight seems to have a pet or something called Spike and guess what? He's a fucking DRAGON. Yup, you heard me right, he's a baby dragon. I'm sleeping in Twilight's house tonight because it's too dark to walk back to my own. Oh and there's apparently no king here, just two princesses and they actually raise the sun and the moon every morning and night! crazy, huh? Twilight's apparently One of the princesses students 'cause she has so much magical prowess. Did I mention the ponies can use magic? There are pegasi, earth ponies (I.E. normal ponies) and magical ponies who have horns (Unicorns, basically) there are things called alicorns and apparently the two princesses are them. They have wings and horns. _

_-Jack Tailor _

Meanwhile, Twilight was getting Spike to address a letter to the princess.

_Dear princess_

_I have made contact with a new species of creature called human. His name is Jack and he appears to have come from another world. He is very interesting and he appears to have some sort of magic emanating from him although I haven't told him yet. He also appears to be very attractive. actually forget that part... he is sleeping in the spare room I have. I told him about Equestria and it seems that he has very different cultures to us. I will tell you more about him tomorrow. _

_-Your faithful student, Twilight Sparkle_

**Well, there's part 2 of my fanfic Anxiety, if you couldn't tell from the last part. I intend to make this a romance fanfic, not sure about adding lemons though... maybe. Anyway, I have a lot of time on my hands so I will be adding chapters quite a lot, I doubt that this story will actually become popular but you never know. A boy can dream, can't he? Anyway once again credit to the magnificent RedOktober for writing the fanfic _Insomnia _and giving me the courage and inspiration to write this story.**

**-Cupzy **


	3. Twilight and Jack

Jack woke up, wiping the sleep from his eyes. He reached for his T-shirt on the counter next to the bed and put it on. Jack recollected what happened yesterday and remembered that he was in Twilight's house. He proceeded to walk downstairs where he saw Twilight reading a book. "Good morning, Twilight." Said Jack, still incredibly sleepy. "Oh, you're up, I was wondering when you would come downstairs." Twilight said with a smile. "What time is it?" Jack asked. Twilight looked at the clock. "It's 10 o clock" Twilight answered. Jack took his rucksack and walked to the door. "I'm gonna go for a walk" said Jack. "Ok, try and get a brief understanding of the town." Twilight answered, eyes still plastered on her book.

Jack stepped outside. It was quite a sunny day today, nobody- or should I say nopony was out, it was pretty early, Jack decided he would check out the outskirts of Ponyville and see if anything interesting was going on. He traveled to the edge of Ponyville and managed to spot a farm out of the corner of his eye. He started to walk towards it. The farm looked like a regular farm you would find on earth, but there wasn't any sign of a pony around. He noticed the sign on the entrance to the farm. "Sweet apple acres." Jack took a look around and noticed that there was a large field of apple trees to one side of the farm. He went to the apple trees and suddenly heard a loud noise, like something just collided with wood. Followed by a rustling sound and something falling and hitting the ground. He found the source of the noise to be a light brown pony, with 3 apples as her cutie mark.

She was wearing a cowboy hat and was using her back hoofs to buck the tree and farm apples. "Um... hi." Said Jack. The pony turned around and looked at Jack oddly, like he was some kind of alien, given that he was a human, that was natural. "Hmmm, well who the heck are you?" the pony said. She had a western accent. "My name's Jack. I was exploring the town and came across this farm." Jack explained. The pin outstretched a hoof to Jack. "Well, it's mighty nice to meet ya Jack. I work at this here farm bucking apple trees to make a profit and feed mah family!" The pony seemed friendly enough and Jack gave her a handshake. "Mah name's Applejack, a pleasure to meet yah" Applejack said. "So, you buck apples, that must be hard work for just one pony to do!" Jack said, amazed by how Applejack could get the apples down from these trees. "Well, ah've got my brother Big Macintosh tah help me." Applejack said. "Well, I'd better get going, I need to get back to Twilight's house." Jack said. "Oh, Yah know Twilight? She's one of mah best friends!" Applejack exclaimed. _"Wow, Twilight sure has a lot of friends..." _"Well I'd better get going, see you later Applejack!" said Jack, giving Applejack a wave. "See yah later Jack" replied Applejack with a smile.

Jack continued walking down the pathway until he found his way back to Twilight's house. He knocked on the door. _"I wonder what I should do now... I've probably met every single one of Twilight's friends..." _The door was answered by Twilight. "Oh, you're back." Twilight said with a smile. "Come on in." she said. Jack walked back into the library. "I'll be right back, I'm just going upstairs to get something." Twilight said. "Ok." Replied Jack. Twilight walked upstairs which gave Jack the opportunity to explore the library more, there were more books in the library than Jack had ever seen in his entire life, he spotted a note on a table at the far side of the library. He figured Twilight wouldn't mind if he gave the note a little read through.

_Dear Twilight_

_I understand the situation with Jack, I have heard that almost the entirety of Ponyville are talking about him. As to your question about magic, anything that exists in Equestria can learn magic, apart from pegasi and earth ponies. Humans, however I do not know about, he might be able to, but I wouldn't tell him, just for safety. As to your sentence where you told me Jack was attractive. I can understand that you could possibly have feelings for him. But he is a human, and you have to remember that, Twilight. I'm sure you will find the stallion of your dreams one day.  
_

_Sincerely Princess Celestia_

__Jack dropped the note, his jaw hitting the floor. _"A pony having feelings for me? Christ, I can imagine how awkward it is for Twilight to talk to me... and what's this about magic, could I learn it? maybe by being in Equestria I could actually use it?" _Jack though to himself. He heard Twilight coming back downstairs, he quickly put the note back in it's original spot and walked away from it. "Ah, there you are Jack! I found a book that might help you with Equestrian history. She dropped a heavy book onto the ground entitled _Equestrian History. _"Oh, thanks! This'll probably help, thanks Twilight!" Said Jack with a grin. "No problem, Jack." Twilight said, hiding a blush.

Twilight looked behind Jack. "Oh, princess Celestia must have replied to my note I sent last night!" Twilight said as she levitated the note toward her. Her eyes stated that she was reading the note, the further she got into the note, the more she started to develop a frown. "Um... Twilight, you okay?" Jack asked, knowing what the note held, this was gonna be awkward. Twilight finished reading the note. "Oh, it's nothing, I assure you." Twilight said, avoiding eye contact with Jack. _"Oh wow, I kinda feel sorry for her. Her heart must be broken. Maybe I should talk to one of her friends about it..." _Jack thought. "Hey, I'm probably gonna go for another walk." Said Jack. "Yeah, ok, that's fine." Said Twilight. Walking upstairs. Jack lifted his rucksack and opened the door. Just as he was about to close the door, he heard the faint noises of crying coming from upstairs. Jack closed the door and decided to go to Rarity's parlor, maybe she would have something to say about this.

He walked to the parlor and knocked on the door. _"Should I really be asking this? Would it just be better to leave Twilight alone? Too late now I suppose"_ Jack thought to himself as Rarity answered the door. "Ah, Jack. Did you bring those dirty clothes you wanted me to wash?" Asked Rarity. "No, can I talk to you about something?" Jack asked. "Well of course, darling! Let me just make you a cup of tea" Rarity said, walking to the kitchen. She came back in a couple of moments with two cups of tea. They sat down at a table. "So, darling, what do you want to talk about?" Rarity asked, sipping her tea. "Well, it's about Twilight. There was this note on her desk from Celestia, telling her that I was the talk of the town right now. But the note also said that Twilight thought I was attractive..." Jack said. Rarity had a hard time keeping this in and almost spilled her tea. "Oh, well that is a predicament..." Said Rarity. "I mean, if Twilight was a HUMAN, I'd probably talk it out with her. but she's not... sooo..." Rarity sipped her tea once more. "Well, personally I think you should talk it out with her." Rarity said. "Yeah, but that would be very awkward" Said Jack. "Well, of course but you might as well, because Twilight's never actually liked anyone before. You don't want to break her heart, do you?" Said Rarity. Jack stood up. "I suppose you're right. I'll talk it out with her... Promise not to tell anyone this, okay?" said Jack. "Of course, darling. I won't tell a soul." Rarity replied. Jack walked out of the parlor. _"This is gonna be so awkward, oh well, at least I can just get it over with..."_

__Jack found his way back to Twilight's house and knocked on the door. Spike answered. "Hey Spike, do you mind if I came in?" Jack asked. "Yeah, sure. Try not to make too much noise, Twilight's pretty upset over something..." Spike said. Jack went inside, the library was eerily quiet, it was like this before, but now Jack knew something was up. He walked upstairs slowly and knocked on Twilight's door. "Hey Twilight? Spike told me you're upset. You wanna talk about it?" Said Jack, knowing full well what was going on. He heard the sound of a bed creaking and hoofs walking towards the door. The door opened and Twilight was standing there, her mane was messed up and it was clear she had been recently crying. "Sure, come in."

Jack walked in. Twilight's room was almost the same as his. Just with more personal belongings. Jack sat down on the bed and urged Twilight to do the same. "So... what's wrong." Jack asked. "Oh, it's nothing, It's just something Celestia said in her last letter..." Twilight said, fighting back more tears. "...What exactly did she say?" Jack said. He knew he had hit the point of no return. "Well, when I got Spike to write my first letter, I kinda said that..." Twilight trailed of before she could finish her sentence. Looks like Jack had to do it for her. "... That I was attractive?..." Said Jack. The room was now filled with an eerie silence. Twilight must know now that he read the note. "You... You knew?" said Twilight. "Yeah, I read the note." Said Jack. Twilight was on the edge of a breakdown. "Yeah... I said that..." She said. "Twilight. you've got to understand that I'm a human, and back in my world, ponies didn't talk, they were just creatures that we kept domesticated, understand?" Jack asked. "Yeah, I understand..." Twilight replied. Jack stood up and started walking towards the door. "I'm gonna go home know. I'll see you tomorrow, ok?" Jack said. Twilight nodded. Jack picked up his rucksack and walked to the door where Spike was. "Hey, can I tell you something?" Spike said. "Yeah, what is it?" Jack replied.

"Earth ponies, pegasi, and unicorns are all considered different species. But that doesn't mean they can't go out with each other, I'm a dragon, I have a crush on Rarity..." Spike explained. "I see what you mean, I'll think about it." said Jack as he walked out the door. He walked back to the everefree forest and back to his house. By the time he was back. It was pitch black and he was ready for bed. He got into his PJ's and took out his Dossier.

_Entry 3_

_I've learned that Twilight has a crush on me, I had a talk with Rarity and then I talked with Twilight. I told her that I read a note that came from Celestia. Apparently Twilight told Celestia that she had a crush on me. But Celestia didn't approve, she sunk into depression when I told her I wasn't interested. Spike gave me a pep talk saying that interspecies wasn't a bad thing. I'm gonna be here for a while and It's only gonna get more confusing from here on out..._

_-Jack Tailor_

__**BOOM! there's the romance part of the fanfic (Still pondering if it should be a clop fiction or not...) but I intend that Twilight will not be the person that Jack goes out with. (Not at the very start at least.) Once again humongous credit to Redoktober for his amazing fanfic _Insomnia_ that inspired me to make this fanfic. I'll probably make some polls at some point (If this fanfic actually gets popular, which I highly doubt)**

**-Cupzy**


	4. The Canterlot Festival

Jack woke up feeling considerably crappy, what did he do yesterday? Oh yeah, he broke Twilight's heart. Jack sighed and got up from bed. Ever since he came to Equestria things haven't been the same. Jack had nothing to do today and he didn't particularly want to go to Ponyville because A) He was still pretty popular with the townsfolk and B) He thought that Rarity probably told everpony about him and Twilight. She seemed like she liked gossip a lot. Jack made himself some toast and sat on his couch, trying to think of something to do. Just as he finished his toast. There was a knock at the door, Jack put his plate down and opened the door. Rainbow Dash was standing there with a grin on her face.

Jack sighed. "What do you want?" Jack said, still angry at her for almost breaking his nose. "Don't you know? the Canterlot festival is this weekend!" Jack was still too sleepy to process what Rainbow Dash was saying. Canterlot was what Jack interpreted as the "Big city" of Equestria, it was close to Ponyville but it would certainly take a while to walk there. "Canterlot festival? What are you talking about?" Jack asked, still half asleep. "It's only the biggest festival of the year!" Said Rainbow Dash, jumping up and down with excitement. "Okay, why are you telling ME this?2 Jack said impatiently. "Because princess Celestia sent all of us VIP tickets to the festival! Including You!" Said Rainbow Dash. Jack was beginning to see the importance of this. "Why would she send me one? She doesn't even know me!" Jack exclaimed. "She wants to see you in person! Princess Celestia and Princess Luna always appear at the Canterlot festival!" Rainbow Dash said.

_"She wants to meet me in person?_ _Why? Is this because of that magic thing I saw in the note?" _Jack thought to himself. "Couldn't you have waited until later to tell me this?" Jack said with a frown. "Well... the Canterlot festival has a rule to it..." Rainbow Dash said. "hm? A rule? what do you mean?" Jack asked curiously. "Well... to go to the Canterlot festival, you have to... take someone with you." Rainbow Dash said. This dumbfounded Jack. "Take someone with you? what does that mean?" Jack asked. He had a vague understanding on what it meant. "It means you have to... like, take someone on a date with you..." Rainbow Dash said. "That's why some ponies don't go, because they don't like all that mushy stuff..." She explained. _"What a weird custom... It's essentially just like a giant prom..." _Jack thought to himself.

Jack and Rainbow Dash stayed silent for a minute. "So... I can't go basically?" Jack said. "What do you mean?" Rainbow Dash asked. "Unless there's another human going to that festival, I can't go. Right?" Jack said. "Well, I was gonna ask if you, um... wanted to go with... me?" Said Rainbow Dash. Jack looked unfazed at this point but his mind was literally exploding with activity. _"Oh, wow. I suppose nothing would happen in the long run if I said no. But it sounds like she's been trying to get a date all morning. She must have asked every stallion in Ponyville." _Jack thought to himself. "...Have any of the other girls got a date?" Jack asked. "Yeah! Rarity, Pinkie pie, Applejack, Twilight, Even Fluttershy!" Said Rainbow Dash. "...Fine." Jack finally said. "Really?!" Rainbow Dash said, now excited. "I've got nothing else to do, when is it again?" Jack asked. "This Saturday!" Said Rainbow Dash. It was Friday today. "Alright, you'd better go to work or something." Said Jack. "Oh no! I'm late!" Shouted Rainbow Dash. She flew away in a matter of seconds.

Jack knew what he was doing today. He took his rucksack. Put on some decent clothes and filled his rucksack with as much dirty clothing as possible. He opened the door and finally managed to get a breath of fresh air. He started walking the path he usually does. He had made landmarks so he knew he was on the right track to Ponyville in case he got lost. After about half an hour of walking, he came to the entrance to Ponyville. He started walking towards Rarity's parlor. After he got his clothes washed he was going to see if their was a Cafe in Ponyville. He knocked on the door of Rarity's parlor. Shortly the door was answered by an over excited Rarity.

"Hello Jack! Are you excited about the Canterlot festival tomorrow?! Only the most prestigious ponies live in Canterlot, I can finally converse with ponies of my class!" Explained Rarity, content with excitement. "Hey, could you wash these clothes for me?" Jack asked as he showed Rarity his rucksack. "Oh of course. Darling!" Rarity said as she dragged the rucksack inside. "Please, come in!" Rarity offered. "Oh, Jack. I have found the most brilliant stallion to take to the Festival with me!" Rarity said. "That's nice, Rainbow Dash told me every one of you found someone to take with you" Jack said. "Oh, Rainbow Dash. The poor thing doesn't have anyone to go with." Rarity said with a hint of sadness in her voice. "Yeah, I decided to go with her." Jack said. "Oh, Jack you're so kind. Rainbow Dash has never went to the Canterlot Festival before! All the stallions in Ponyville find her far too tomboyish" Rarity explained. "I see" Jack said.

"Well darling your clothes should be done in an hour or so. Come back and I'll give you them back." Rarity said. "Thanks for the help, Rarity." Jack said as he gave Rarity a wave. He closed the door behind him and started to search for a cafe. It was lunchtime and he was starving. He eventually came across a small cafe at the corner of town. He sat down at one of the empty tables, finally able to get some peace and quiet he waited for the waiter to come and take his order. He waited about five minutes before he heard someone sitting down at the opposite end of the table. It was Applejack. "Well, ah never expected you to be hear, Jack! It's nice tah see yah." Applejack said with a smile. "It's nice to see you too Applejack. Are you excited for the Canterlot festival?" Jack asked just as the waiter approached them. "May I take your orders?" The waiter asked politely. "Ah'll have a salad please." Applejack responded. "I'll just have tea and a salad, please." Jack said. "Now what where we talkin' about?" said Applejack.

"I asked you if you were excited about the Canterlot festival coming up." Jack explained. "Dang right ah'm excited for the festival. All the rival farms compete against each other to see who can make the best cider! Ah'm going with this boy from another farm in Canterlot! Wait, are you goin' too Jack?" Applejack asked. The waiter showed up with their food. "Yeah, I am" Jack said "With Rainbow Dash" he continued. "Aww that's so cute!" said Applejack. "Thanks, I suppose. Well, I'd better get going. He finished off the last of his meal and started walking back to Rarity's parlor. On the way there he spotted Fluttershy with a stallion walking beside her. He decided to try conversation again, It didn't work out so well last time.

"Hey, Fluttershy!" Jack shouted. Fluttershy looked in Jack's direction and cringed a little. _"Hm, she must still be sour from when I scared her off in the forest..." _Fluttershy walked up to Jack in a slow manner. "Um... hi Jack. Twilight told me about you and said you were a really nice guy..." Fluttershy said, ever quiet. "Well, I'm just happy to see you're not still angry at me for scaring you." Jack said. "Oh it was nothing Jack. I just get frightened easily..." Fluttershy explained. "Are you excited for the Canterlot festival?" Jack asked. Fluttershy's face immediately lit up. "Oh yes! I can't wait to see all the animals preserves in Canterlot, It's going to be lots of fun! I met this really nice stallion and he's going to the festival with me... I mean- if it's alright with him..." she said. The stallion that was standing next to Fluttershy looked older than her. He was a white pony that had a long, red mane that went down the large majority of his back. he was a pegasi. "That's cool, well, I'll see you around Fluttershy!" Jack said as he continued walking towards Rarity's parlor

Just as he was about to reach Rarity's parlor a pink pony jumped at him from a nearby bush and tackled him to the ground. For a really short pony they packed a punch. "Ow! Jesus christ!" Jack said as he got back up. Pinkie Pie was standing in front of him. "HeyJackareyouexcitedfortheCa nterlotfestivalIcertainlyamt heymakethebestcupcakestherea ndIfoundthisreallycoolstalli onwhosaidhewouldgowithme" Pinkie Pie said in a jumble of words that Jack could barely understand. "Ok, I'm gonna head home now, Okay?" Jack said. _"Jesus, she explained everything to me in under two seconds..." _Jack thought "Okay Jack see you tomorrow!" Pinkie Pie gave a huge wave as Jack walked away from her.

Jack managed to find Rarity's parlor and It was getting pretty late. He knocked on the door which was answered in moments by Rarity. "Oh hello Jack, I washed your clothes for you!" Rarity said as she handed Jack his rucksack. "I'll see you tomorrow Rarity!" Jack said with a wave. He wandered down the road until he found the path that leaded back to the Everfree forest. After about half an hour he got back to his house. He was exhausted. He changed into his PJ's and took out his Dossier.

_Entry... 4? I don't know_

_Turns out there's a big festival tomorrow in Canterlot (which is essentially the London of Equestria) but you can't go without a date. So I went with Rainbow Dash. (I know, going out with a pony. Crazy, right?") princess Celestia wants to see me at the festival, I don't know why but I think it has something to do with the note that I read yesterday. Every one of Twilight's friends had a stallion to go with. I never saw Twilight the entire day, though. I wonder where she is... Oh well, I think tomorrows gonna be an interesting day. To say the least._

_-Jack Tailor_

__**Okay, so there's the last chapter I'm gonna write today. wow, this took up pretty much my entire day. It's not like I had anything to do anyways. Once again credit to Redoktober for inspiring me to write this fanfic. My friends are wondering what the hell I'm doing in my spare time. (They don't know I'm a brony, or a fanfic writer. If I told them I'd probably lose the majority of them) So... yeah, I plan to make this a JackxRainbowDash before I make it a JackxTwilight.**

**-Cupzy**


	5. The ACTUAL Canterlot Festival

Jack woke up pretty early this morning. Today was the day of the Canterlot Festival. Rainbow Dash hadn't told him the exact time they should be going so he decided to stay in the house until she showed up. Jack looked at his alarm clock; 11 o clock. Jack got up, went downstairs and made himself some cornflakes. The usual stuff. After finishing his lunch and getting himself dressed, he finally heard a knock at the door. He opened the door to reveal an over excited Rainbow Dash. "Hey Jack! are you ready for the Festival?" Rainbow Dash said excitedly. "Yeah I'm ready, can I just make one thing clear?" asked Jack. "Yeah? What is it?" Rainbow Dash wondered. "This is not a date, this is simply so I could see the princess, okay?" Said Jack. Rainbow Dash pondered over what Jack just said. _"huh, I at least wanted to have a nice time with him..." _Thought Rainbow Dash. She nodded and motioned for Jack to follow her. Finding Ponyville didn't take as long due to Rainbow Dash's flying abilities. They made their way back to Ponyville in record time and found all of their friends waiting in front of Twilight's house.

Everypony was there, standing next to their date. The first thing Jack noticed was that Twilight was there. She was giving him an odd stare, something like sadness mixed with anger. "Hi everyone!" Said Rainbow Dash. "Wait, how are we getting to Canterlot?" asked Jack. "Oh, we're being taken there on chariots." Rarity explained. _"Wait, chariots!? Aren't those the things that are PULLED by Ponies?" _Thought Jack. Just then, he heard the noise of wheels approaching. Sure enough, there were two male stallions in armor dragging along a golden chariot. "That thing looks like something I would never be able to afford..." Said Jack. "Yeah, but we got VIP tickets, we're being given the best Equestria can offer!" Said Rainbow Dash. There were multiple chariots. One being able to hold at least 4 ponies (or, in this case, humans.) They piled into the chariots. Jack and Rainbow Dash were accompanied by Fluttershy and her date. According to the stallions pulling the cart. The ride would take around two hours. They had plenty time to waste. "So, are you guys excited for the Festival?" Asked Jack. "Oh yes, I can't wait to see all the animals!" Said Fluttershy. Even excited, she was still as quiet as a mouse. "Hey, Jack?" Asked Rainbow Dash. "Yeah?" Replied Jack. "Did you see Twilight when we were waiting for the ride to come? She was giving you a weird look..." Said Rainbow Dash. _"She couldn't possibly be still be thinking about that. We had a talk and she seemed to understand. Maybe it's because she saw me with Rainbow Dash, maybe she thinks we're..." _Thought Jack.

After about an hour and a half into the ride, Canterlot could be seen in the distance. It was huge, but not as big as the city he was used to. By the time they reached Canterlot they could see party decorations plastered all across the City. They were dropped off in a large plaza in the middle of the city. By the time Jack stepped out he noticed a few ponies looking at him. Had the news spread to Canterlot about a human in Equestria yet? Either way Rainbow Dash had already flew away to enjoy the festivities. _"I might have a look around as well, I suppose." _Thought Jack.

This gave Jack a chance to explore the City. There was certainly a lot of activity. Some ponies were apple bobbing. Some fillies were skipping along merrily. Everpony was having a great time. As Jack was sightseeing, he didn't look where he was going and walked into a pony. Naturally, he expected the pony to fly back fifty feet, but instead he was completely knocked over. He looked up to see a gigantic pony. The pony had extremely dark blue skin and her mane looked like it was made out of the night sky. That's when Jack realized. The pony had both a set of wings and a horn, it was an alicorn! Jack rose to his feet. "I'm sorry for walking into you, I wasn't looking." Said Jack. The pony wasn't fazed at all by the incident. Her facial expression only changed when she looked at Jack. "Oh! you must be Jack." Said the pony. "Yeah, that's me, who're you?" Asked Jack. "My name is Luna, you may know me as princess Celestia's sister." Said Luna. Jack's jaw dropped. _"I just walked into one of the most powerful figures in Equestria!" _Thought Jack.

"It's a pleasure to meet you." Said Jack. "There's no need for pleasantries, my sister wants to see you right away!" Said Luna. "Yes, of course! Lead the way." Said Jack. They walked back to the plaza, talking along the way. "Twilight told me about you and your sister. You're the one who raises the moon, right?" Asked Jack, still worried that he might cross the line of privacy. "Yes, that's me, Celestia has been telling me that you have had some trouble with Twilight?" Asked Luna. "Uh... yeah, we had a little run-in. But I'm sure she's forgotten about it." Said Jack. They found their way back to the plaza. "Looks like we're here in time for the announcement." Said Luna. Just as she finished her sentence a brown pony with a sash over her body walked to the center of the plaza.

"Fillies and gentlecolts! As mayor of Canterlot, I hereby present to you... Princess Celestia!" Said the mayor as a platoon of guards entered the plaza. They formed two lines on either side of the street and bowed their heads as a white pony with blue hair and a necklace stepped into the plaza. She was an alicorn, Like Luna. "Go on, talk to her!" Said Luna. Jack could barely take a step towards the princess without being surrounded by royal guards. "Guards! lower your weapons!" Ordered Luna. The guards followed orders and stepped back so Jack could talk to the princess. "Ah, you must be Jack, I wanted to talk to you about something that was passed on to me in a letter Twilight Sparkle sent me. Jack just stayed silent.

"In the last letter she sent me, Twilight Sparkle said that she had feelings for you... I understand that this may be an awkward situation for you, but ever since you told her you weren't interested. She has sunk into depression." Celestia explained. "What exactly do you want me to do Princess?" Replied Jack. "I was hoping that you could... There's no easy way to say this Jack, _Go out with Twilight?" _Jack pondered over the situation. "Yeah, okay. I'll give it a try, princess!" Said Jack. "I appreciate your concern for Twilight, Jack. And please, call me Celestia." She said with a smile, walking off to converse with some of the guests. Luna walked up behind Jack. "This must be awkward for you, right?"

"Well, I- uh..." Stuttered Jack. Luna seemed to be the most laid-back out of the two. She had no problem conversing in the same way that Jack did. "It's no problem. You only have to do it for a day or so." Luna said. "Yeah, I suppose it isn't that bad." Replied Jack. He continued enjoying the festivities until it was late at night. The golden chariots were back and ready to take the ponies back to their homes. Jack piled in with Rainbow Dash along with Twilight. Along the trip home. Twilight had a certain happiness around her. It seemed that Celestia told her about the plan, and she was pretty excited about it.

By the time they were dropped off in Ponyville. It was very late at night. Everypony said their goodbyes and left for bed. Jack started walking back to his house when he was stopped by Rainbow Dash. "Hey, no goodbye?" Rainbow Dash said. "I thought we made it clear this morning, that was not a date." Replied Jack. "Ah, come on. At least give me a kiss goodbye?" Rainbow Dash said, pulling her best "innocent" face. "Fine." Jack said. Jack closed his eyes and leaned in for a kiss. He was answered with a quick peck on the cheek. "You know, you aren't that bad Jack. I'll see you tomorrow, ok?" Rainbow Dash said as she flew away. Jack smiled and started walking back home. It was past midnight when he eventually reached his house. He put on his PJ's and took out his dossier.

_Entry... 5?_

_Today was an interesting day, I got to meet the princesses for the first time. Celestia had a talk with me and persuaded me to go out with Twilight for a day or so... When we came back, Rainbow Dash gave me a kiss on the cheek and then flew off. Don't tell me she likes me too? Ah, well. It's pretty late and I'd better get to bed. Peace._

_-Jack Tailor_

__**So, I only uploaded this chapter today. Why? because I decided that's what I'm gonna do from now On! Once again credit to RedOktober for inspiring me to write this fanfic. Is it just me or do these stories get shorter every time? Well, maybe I'm just running out of ideas... I intend to make this fanfic go a bit like this: MikexTwilight followed by MikexRainbowDash followed by (Should I make it this long?) Mikex?**

**-Cupzy**


	6. Jack and Rainbow Dash

Jack woke up. Yesterday was a long day. He looked at his alarm clock. 1 o clock. Great, no time for breakfast. He got up and put on some clothes. _"Better get this Twilight thing done before I regret it..." _Said Jack as he threw his rucksack over his shoulder and opened the door. Not realizing that Rainbow Dash was standing right there, he lifted one foot and kicked her right in the face. Sending her flying backwards. "Oh, shit! I'm sorry!" Said Jack as Rainbow stood back up. "Hey! what the heck, Jack?!" Said Rainbow Dash. Rubbing her now bleeding nose. "I think I've got some bandages in my kitchen. I'll be right back!" Said Jack as he hurried to the kitchen. He opened his drawer and took out his first aid kit. He took some bandages out of it and ran back to Rainbow Dash. "Here, let me put this on." Jack said. He put the bandage on. "Thanks, Jack." Rainbow Dash said. "No problem, you're my friend after all." Jack said. Rainbow Dash blushed. "Well, I came here to see if you, like... Wanted to do anything today" Asked Rainbow Dash. "As much as I would love to, I have to go talk to Twilight today, sorry." Explained Jack.

"Oh, okay." Said Rainbow Dash. She flapped her wings and flew away without saying a word. Jack shrugged and continued walking towards Ponyville. _"Why would the princess ask me to do this? Does she really care for Twilight that much?" _Jack thought to himself as Ponyville became visible in the distance. By the time he got there it was 2 o clock. He started walking towards the library. He knocked on the door and waited for an answer. Spike came to the door. "Oh, it's you Jack! Come on in!" Said Spike. Inside the library he could hear Twilight shuffling through books. He looked through the bookcases until he found Twilight studying books on a table. "Uh... Hey Twilight..." Said Jack. Twilight turned around and saw Jack standing there. "Oh, hello Jack!" Twilight said. Closing her book. "Um... Do you remember the talk we had a couple of nights ago?" Asked Jack, hoping not to bring up any bad memories._  
_

"Oh, Uh... Yes, I remember..." Twilight said, a frown starting to develop on her face. "Well, I've been thinking about it and I've kinda..." Jack trailed off before he could finish his sentence. "You've decided what?" Asked Twilight curiously. "Uh... I kinda... Changed my mind?" Jack said, acting almost as shy as Fluttershy. "..." Twilight didn't speak. A silence filled the room. "Does that mean you want to...?" Asked Twilight. "Y-Yeah..." Replied Jack. He could see the smile start to develop on Twilight's face, she was excited, she just wasn't showing it. "Ok then, I forgive you." Said Twilight. "Okay..." Said Jack. "So... do you wanna do something?" Said Jack. "I don't know. Do you want to go down to the cafe?" Asked Twilight. "Yeah, that sounds like a good idea." Twilight said with a smile.

They found their way to the cafe and sat down at one of the tables. A waiter came shortly after to get their orders. "May I take your order?" Said the waiter. "I'll have a salad please." Answered Twilight. "I'll just have a cup of tea." Said Jack. The two sat in silence for a while. Jack hadn't really thought this through. "So, uhh..." Jack stuttered, he was trying to find a good conversation topic. "Do you read?" asked Twilight. Jack used to spend quite a lot of time reading back in London. "Yeah, reading took up quite a lot of my time." Replied Jack. At least they had something in common. The water came with their meals. "I've been addicted to reading ever since I was a fillie." Twilight said with a smile.

_"Although she's a pony, I don't see anything wrong with going out with her. She's nice." _Jack thought to himself. "Oh, look at the time. I really must be going. I'll see you tomorrow, Jack!" Twilight said as she finished her meal and walked off. Jack had nothing else to do today. _"I haven't seen Applejack in a while, maybe I'll go visit her." _Jack thought to himself. He started walking through Ponyville until he could see Sweet apple acres in the background. He came to the farm's entrance and saw Applejack bucking trees. "Hey! Applejack!" Jack shouted. Applejack turned around as Jack walked towards her. "Oh, hey there Jack. What brings ya here?" Applejack asked. "I was just going around the town and figured I'd visit you." Explained Jack.

"Well, that's mighty kind O' ya, by the way Jack, could ah ask ya a question?" Said Applejack. "Sure, what do you want?" Replied Jack. "Well, Twilight Sparkle's been goin' around town all happy and that, she shouted somethin' about you and her?" Said Applejack. "Are you... doin' something with her?" Asked Applejack. "Oh, um... we're kind of, um... how should I put this... going out?" Said Jack. Applejack's face lit up. "Oh, wow! Congratulations Jack!" Said Applejack. "Heh, thanks." Replied Jack. "Well, Ah'm sure you've got some more important things tah be doing other than talking tah little ol' me" Said Applejack. Jack nodded and walked off. It was getting late. He'd better start getting home. He started walking in the direction of the forest. But was cut off halfway by Rainbow Dash. "Oh, hi Rainbow Dash! How are you?" Asked Jack. She had a strange look on her face. "How am I? What's this I've been hearing about you and Twilight?" Said Rainbow Dash. "Oh yeah! We're um... going out now." Explained Jack. He barely had time to react before Rainbow Dash threw a punch right for his face. For a little pony. They sure packed a lot of power.

Jack was knocked over. He fell backwards onto the dirt road that led to the Everfree forest. "Ow! Shit, why did you do that?!" Said Jack, rubbing the side of his face. Rainbow Dash had a stern look on her face. "I thought you liked me?" She said. "Twilight was in depression so I felt sorry for her, ok?" Said Jack. "And that's a reason you can just DITCH me? Said Rainbow Dash. "What ever gave you the idea that I liked you?" Said Jack angrily. "B-but... Last night..." Said Rainbow Dash, tears starting to form in her eyes. "I was worried that you would take that the wrong way." Explained Jack. Rainbow Dash wasn't about to cry in front of Jack, she flew away before drawing a tear and left Jack there, alone with his thoughts. _"Ah, shit. Her too? Who knew living in Ponyville would be so stressful..." _

He got back up and brushed his face once more. _"Guess I'll have to let fate decide..." _Thought Jack. He started to walk inside the Everfree forest. He thought he would be here for a couple of days and then he would just... Go back to earth. He never expected relationships to come into this. He found his house and sat down on his bed. _"This shouldn't be so tough to work out, right? I'll just have a few more days with Twilight and then move on to Rainbow Dash. Simple." _He put on his PJ's and took out his dossier.

_Entry 6_

_I did as Celestia asked me and went out with Twilight. Everything was going well until I came home tonight. Rainbow Dash stopped me and punched me square across the face. She wasn't happy with me going out with Twilight. tried to explain to her but she flew away once I had started. Hopefully I can wait this out and see what happens. It'll probably work out in the end... Right?_

_-Jack Tailor_

__**NEW PLOT POINT ACTIVATED. PLEASE INSERT SHITTY CHAPTER HERE. Well anyway. That was kind of an empty chapter. I promise I'll make it more interesting tomorrow. Once again credit to Redoktober for inspiring me to write this fanfic. I know I fucked up my system from last chapter but hey, I'm keeping it fresh. Right? ...**


	7. A night with Rainbow Dash

Jack yawned and lazily sat up on his bed. He looked at his alarm clock. 8 o clock. Yep. This was gonna be a long day. He stood up and got his clothes on. A black T-shirt with jeans. Over the time Jack spent in Equestria he has also grown considerable facial hair. He had a shaver in the bathroom and he managed to make it into a goatee (After several bandages and bleeding) He went downstairs and thought to himself that maybe the forest wasn't a great place to live. He could relocate to Ponyville. He made himself some toast and sat down. After finishing his breakfast he went upstairs to grab his rucksack and came out of his house to go to Ponyville. He knew the route by heart now. And he seemed to get faster every time he did it. This time it only took fifteen minutes. He had no idea what to do today. He certainly didn't want to see Rainbow Dash today so he went to the library to see Twilight. He walked down the streets of Ponyville until he reached the town library. He knocked on the door and waited for a response.

For once, Twilight actually answered the door. "Oh, hello Jack!" She said, her face lighting up as soon as she saw Jack. "Hey Twilight, it's nice to see you too. I was wondering if you wanted to do something today." Said Jack. "Well, I was going to get everyone to come over tonight for dinner. Do you want to help me prepare?" Asked Twilight. Unbeknownst to Jack, Twilight wasn't planning on making it a dinner party, but rather a discussion about Jack and how everyone gets along with him. "Yeah, sure. I'll help you." Said Jack. So he spent the rest of the day setting things up, making food etc etc. Until they managed to get the preparations finished by lunchtime. "This is looking great! Thanks for all your help Jack!" Twilight said with a smile. "It's no problem Twilight." Jack said, smiling back. "Well, I'd better get going. I need to get something to eat." Said Jack. Just as Jack was about to open the door. Twilight grabbed his hand and pulled him back into a kiss. Jack was surprised but didn't mind. They kissed for a few seconds before finally pulling back out. Jack and Twilight both smiled at each other before Jack stepped outside of the library. _"I kissed a horse... Score..." _Jack joked to himself in his mind. He started to walk towards the cafe. Halfway through his walk. He felt rain fall onto his forehead and looked up. There was a single rain cloud above him. After a slight impact noise. The rain picked up to almost drenching level and got his entire attire soaked. "Ah, christ. At this exact point and time I must have been pretty unlucky for that to happen."

He stood out of the rain cloud and looked up. Rainbow Dash was sitting on top of the cloud, with a smug grin on her face. Jack clenched his fist and pointed up. "Hey! I see you up there!" Jack shouted. Rainbow Dash just sat there, not listening to a word Jack was saying. "If this is about yesterday I'm sorry, Okay?" Jack shouted to Rainbow Dash. "If I hurt your feelings I'm sorry!" Jack continued. RD peeked her head over the cloud. "If you're sorry why don't you just go out with me?" Said RD. "B-but I have Twilight already! All you're doing is making this more complicated!" Jack said as he shook his hair to dry it off. "Do you know how stupid you look right now?" Rainbow Dash shouted. Jack paid her no attention and simply walked in the opposite direction. _"Persistent bitch..."_ Jack thought. He continued walking through Ponyville until he finally came to the cafe. He took a seat and put his head on his hand. _"God, this is confusing. I really need to decide what to do..."_

Just as the waiter came along. RD flew down from the sky and sat on the opposite side of Jack. The waiter decided to leave them to their troubles. "What do you want?" Jack said. "I think we need to talk." Said RD. "We already had a talk, five minutes ago." Explained Jack. "Come on... I like you. Why don't you like me back?" Asked RD. "Because A) I have Twilight and B) You won't leave me alone." Said Jack. "Why can't you just, Like, go out with both of us?" Asked RD. "Because That's cheating." Explained Jack. "Come on. Why don't you come over to my house tonight?" Asked Rainbow Dash, moving her hoof towards Jack. He could see what she was getting at. "How about no?" Said Jack, Pushing her hoof away when he said "no." "Aw, come ooooon, It'll be fun." Said RD, pulling her best puppy dog face_. "_Only if you promise not to do any funny stuff, besides. Don't you live in the clouds?" Asked Jack. "Funny stuff? Ewww... How could you even THINK that Jack?" RD said, visibly trying to keep from smirking. "Besides, You could just get one of the chariots that go to cloudsdale." RD said. "Alright, fine. You're on." Said Jack.

"Great! come over whenever!" Said RD before flying away. Jack knew this wasn't the time for lunch anymore. _"I know she's gonna try something. You just watch." _As he continued his walk around Ponyville. He managed to waste time until about 6 o clock. He figured that this was a good time to visit Rainbow Dash. Meanwhile, in the town library. Twilight Sparkle was greeting everyone that came for dinner. They all sat down at a big table that Twilight and Jack moved to the middle of the library. Everypony got a helping of Jack's cooking. "Alright, I've called you all here to talk about Jack." Twilight said. "Oh, Didn't Jack say something about you going out with him?" AJ said. "Yes, but-" Twilight was cut off by all of the ponies Awwwwwww-ing at her. "That's so sweet Twilight!" Said Rarity with a smile. "Yes, well anyway. I wanted to know what you girls thought about him?" Said Twilight.

"Oh, he is simply a darling! The boy is so polite!" Said Rarity. "Yeah, he seems alright. Ah say he's pretty dang likable!" Said AJ. "He seems okay... he's a little scary though..." Said FS. "He's really cool. And Nice! I hope he likes cupcakes!" Said Pinkie. Everypony seemed to like him with little to no flaws. "Wait, where's Rainbow Dash?" Asked Twilight. "I've got no Idea, she told me she had some important stuff to do!" Said Pinkie. "Hmm... I hope she's alright..." Twilight said. Back into Jack's perspective, he had just gotten on to a Chariot that was bound for Cloudsdale. The chariot got to it's destination In around half an hour. Cloudsdale was pretty big. It was on a cloud. (Well, what were you expecting?) and there were rainbows all over the place. He got dropped off and he went to go find Rainbow Dash.

He found a large plaza-like area where he saw RD waiting for him. "Hey! Rainbow Dash!" Shouted Jack. Not many people were out. And it was pretty deserted. RD turned around and saw Jack. "Oh there you are. I thought you would've gotten lost." She said. "Well, let me show you to my place." She continued. They walked along a road until RD stopped at a house. "Try to wipe your shoes on the way in." She said. And opened the door into the house. Jack was amazed, almost everything in the house was made out of clouds. "I hope you like my house." RD said. Jack sat down on one of the chairs. It was extremely comfortable. Better than anything he ever owned. "Wow! This is really comfortable!" Said Jack. "Yeah, everyone that's been in my house says that, do you want some dinner? You must be hungry!" Said RD, "Yes, please." Said Jack. Maybe RD wasn't so bad after all.

She came through a moment later with a plate of various vegetarian foods. Although Jack preferred meat, he wasn't picky. The food was delicious. After half an hour of eating, Rainbow Dash finally spoke up. "Do you want to stay here tonight? At this time of night, It'll take you ages to get a Chariot ride home." RD offered. "Yeah sure. I'm pretty tired. I'll probably get ready for bed." Jack said. He walked upstairs into an empty bedroom with nothing but a bed in it. He put his rucksack on the floor and put on his PJ's. He got into the bed. it was the most comfortable thing he had ever slept in! He took out his dossier.

_Entry, I dunno. 10? No. 5? No. 7! That was it!_

_RD (Rainbow Dash) Talked me into sleeping at her's tonight, I don't know where Twilight is. But this bed is one of the most comfortable things I've ever slept in! The other thing being RD's Chairs. I didn't do much else today, but RD isn't acting the way I thought she would. I can sense a nice friendship with her! _

_-Jack Tailor_

**HAH! I BET YOU WERE EXPECTING SOME SORT OF DIRTY DIRTY EXPLICIT SCENE, RIGHT? well no. I was originally gonna make this a clopfic but then I said "No" and deleted a paragraph I just wrote. Once again, credit to Redoktober for inspiring me to write this fanfic. This may just be me, well. Probably not,but I think I'm ripping off Redoktober a little too much. What do you guys think? (Haha, look at me. Acting like I have fans) Peace.  
**

**-Cupzy**


	8. Conflicted Feelings

Jack woke up. But didn't want to leave the bed. It was the most comfortable thing he had ever slept in. _"I'll just wait until RD comes to wake me up" _Thought Jack. He dozed off once more until he was awoken by the sound of RD's voice. "Hey!" RD shouted at Jack with a grin in her face. Jack simply waved her away. "You're so lazy! And that's coming from me!" RD exclaimed. She nudged her hoof under the cover and punched Jack. He sprang out of the bed. Holding the side of his torso. "Ow... Why'd you do that?" Asked Jack, who was in some pain. "Don't think I'll let you sleep in all day!" RD exclaimed with a giggle. Jack got up and looked at the time. 1 o clock. Wow, he had really slept in this time. "Well, I suppose I'd better get going." He said as he put on some decent clothes.

"I'm going to catch a chariot back to Ponyville. Don't you have work or something?" Asked Jack as he slung his rucksack over his shoulder. "Nah, I've got the day off today. I could come down with you if you want." RD said. "That's okay. You probably have better stuff to do than hang around with me all day." Jack said with a chuckle. "Yeah, I suppose I don't have time to hang around with a loser like you." RD said, before bursting out in laughter. Jack paid her no mind and continued walking down the road to the chariots. After about half an hour he finally managed to get a chariot that was going back to Ponyville. The ride back didn't take any longer than the first one. And he was at Ponyville in no time.

He had nothing else to do today. So he started to head to the town library. Maybe Twilight had something interesting for Jack to do. He walked towards the library and knocked on the door. Spike answered. "Oh hey Jack! Twilight was just looking for you." Exclaimed Spike. Jack walked inside and saw Twilight studying on a table. She turned around when she heard Jack coming. "Oh hello Jack! I wanted to ask you something." Said Twilight. "Sure, what do you need?" Replied Jack. "You know how I had dinner with my friends the other day?" Asked Twilight. "Yeah, what of it?" Replied Jack. "Well... Rainbow Dash wasn't there, do you know where she was?" Asked Twilight. _"Oh, she was at her house when I went over... But I don't want Twilight to take that the wrong way." _Jack thought to himself. "No, I didn't see her the whole day." Jack lied.

"Oh, okay. I'm just worried about her." Said Twilight. Jack sat down next to her. "I'm sure she's fine." Jack said. "Thanks. Anyway, there was something else I wanted to talk about." Said Twilight. "It was about our relationship..." She continued. _"She always acts like Fluttershy when she talks about that..." _Jack thought. "Do you think it's... working out?" Asked Twilight. _"This could be my chance to break up with her... But would it hurt her?" _Jack thought. "I mean, if you say no. I don't have any problem with breaking up..." Twilight continued. "Well, I think it would be for the better if we broke up... I'm just afraid of hurting your feelings again..." Explained Jack. "I understand. I'm over it now." Twilight said. "So does this mean you want to..." Twilight stuttered. "K-kinda... yeah..." Jack said. The silence that filled the room days ago came back again. Twilight had an odd look on her face. "I understand Jack." Twilight said, turning back to her books. Jack went back to the door slowly. At least she took it well...

Jack now realized that he was once again bored with nothing to do. He started walking around town. Trying to get a better layout of Ponyville. As he was exploring the town he saw RD walking around Sugercube corner. "Hey! Rainbow Dash!" Jack shouted. She turned around. Her face showing a smile when she saw Jack. He walked up to her. "What's the matter? Can't get enough of me?" RD said giggling. "Very funny. I was just wondering what you were up to." Jack said. "You're acting more... Open than usual... What's happened?" RD asked with a peculiar look. _"Damn, she caught on quick..." _Jack thought to himself. "No, nothing happened. I just... Uh-" He was cut off by RD. "Wait, did something happen between you and Twilight?" RD asked. With an excited look on her face. Jack took a deep breath.

"We kinda... um... B-broke up." Jack said. RD was on the edge up until now. She jumped up into the air shouting "YAHOOOOOO!" Until she came back down. "This means you can go out with me now, right?" RD said, cutting right to the chase. "No, that would be unfair on Twilight." Jack said. RD was still persistent. "Well, at least you can go out with me at some point, right?" RD said. _"She keeps asking. How many times do I have to tell her I'm really not interested?" _Jakc thought to himself. "Look, we can talk about this tomorrow, ok?" Jack said. Right now all he wanted to do was get away from her.

"Oh, okay!" Said RD who happily flew away. Jack decided to go to Rarity. Maybe she had some advice for the situation. He walked towards her parlor and knocked on the door. Rarity answered in a few moments. "Oh hello Jack! Do you need anything?" Rarity Asked. "Can I talk to you about something?" He replied. "Of course darling! Come in, come in." Rarity said. Jack sat down at a table. Rarity came through moments later with two cups of tea. "So, what do you want to talk about?" Rarity asked. "Well, first of all. Let me just say that me and Twilight have kinda... well... Broken up." Jack said. This ensued a gasp from Rarity. "Really? But you two were such a good couple..." She replied. "Yeah, but I think that Rainbow Dash might have a crush on me... She won't leave me alone..." Jack said. "Rainbow Dash has never had a lover before. No wonder she's desperate." Rarity said, sipping her tea. "Yeah, but she's being so persistent. I've tried talking to her and telling her I'm not interested. But she keeps asking me. It's really starting to piss me off..." Jack said. "Personally I think you should give it a go. Rainbow Dash really needs someone in her life and, don't take this the wrong way Jack. But you are quite a catch." Rarity said.

"I appreciate the help Rarity. I'll probably try to talk to her about it tomorrow. I'll keep your advice in mind." Jack said as he stood up and exited the parlor. It was about 5 o clock. He still had plenty time left to waste. _"Might as well catch up with the other ponies." _Jack thought to himself. He started walking towards Fluttershy's house. He had never actually been inside there yet and he was pretty curious of what kind of life Fluttershy actually lived. He went up to her house and knocked on the door. After a few minutes Fluttershy finally answered the door. "Hey Fluttershy." Jack said. "Oh, hello Jack, would you like to come inside?" Fluttershy asked. "Yes please." Jack replied. Fluttershy's house was quint, to say the least. There were several birdhouses on the walls and there were stairs leading to the next floor. "This is a nice house." Jack said. "Thank you." Replied Fluttershy. The two sat down and started to chat.

"So what brings you here Jack?" Fluttershy asked, ever quiet. "I just decided to visit all the ponies I hadn't seen in a while." Replied Jack. "That's very nice of you, would you like to see some of my animals?" Fluttershy asked. "Sure, I always liked animals." Replied Jack. Fluttershy sure had a lot of animals. She showed him around the outside of the house and introduced him to the various animals that she kept. Eventually the clock hit 7 and Jack said goodbye to Fluttershy. He decided to go visit Pinkie Pie. Who he assumed was at the cupcake place. He stopped by the cupcake shop and sure enough Pinkie Pie opened the door to greet him.

"Hey Jack! What brings you here?" Said Pinkie. "I was just sightseeing." Replied Jack. "Oh hey! Do you want to taste my new batch of cupcakes?" Asked Pinkie. "Sure." Said Jack. Pinkie brought him inside where she showed Jack the new batch of cupcakes she had just made. _"Jeez, I knew she had a lot of energy But Jesus. She must make these all night..." _Jack thought to himself. He took one of the cupcakes in his hand and bit into it. The amount of chocolate that went into his mouth was unreal. But it was tasty nonetheless. After eating a couple more of the cupcakes Jack bid farewell to Pinkie and started walking to his house.

On his way to the Everfree forest he heard a familiar Fwoosh-ing sound and RD landed in front of Jack, scaring him. "Ah! Stop jumping at me in the middle of the night!" Said Jack. RD was rolling on the floor crying her eyes out. "Hahaha! you should have seen the look on your face!" RD said to Jack between fits of giggles and laughter. Jack stepped over RD and continued to walk towards his house. Being discreet certainly wasn't RD's thing, as Jack could hear her following him. He merely ignored her and continued walking through the Everfree forest. When he finally reached the door he spoke up. "Are you gonna leave me alone now?" Jack asked. "What? How did you see me?" Said RD. "Believe me, I could hear you from a mile away." Jack said with a chuckle. "Hey could I stay at your house tonight. "If you do you're gonna have to sleep on the couch" Jack said. "It's no bother!" RD replied. He opened the door and RD sat down on his couch. "Huh, this thing isn't as comfy as my couch." Said RD.

"We don't make things out of clouds on earth." Replied Jack. He went upstairs and put on his PJ's. He took out his dossier.

_Entry 8 (Aka the TLDR section)_

_So I broke up with Twilight today. Yeah, all good things have to come to an end. RD is staying over at my house tonight, she's sleeping on the couch. I caught up with all of Twilight's friends today, I also had a talk with Rarity about RD, she said that I might as well try it. I'll have a think about it tomorrow. Hopefully these ponies will have a breakthrough in human - sentient pony communication soon._

_-Jack Tailor._

__**Oh noes, Jack broke up w/Twilight. W/ever shall we do? Anyway that was today's chapter of Anxiety, Nothing really too important to bring up right now. Credit to Redoktober for giving me inspiration and courage and stuff. Peace.**

**-Cupzy**


	9. Rainy Days

Jack yawned and sat up in his bed. He slowly put some clothes on and went downstairs. He set his alarm to wake him up at 10 o clock. He went downstairs and almost crushed Rainbow Dash when he sat down. She was fast asleep. Jack sat on the end of the couch where she wasn't sleeping and almost dozed off again. He pulled himself together and went to go get some cereal. He made two bowls of cornflakes, he placed one on the table and started eating the other. When it was apparent that RD wasn't going to wake up, he punched her in the stomach. She woke up with a scream that killed Jack's eardrums. "Good morning." Jack said, his mouth half-filled with cornflakes. "Why'd you wake me up?" Said RD, rubbing the sleep out of her eyes.

"If you complained about me sleeping in, then I'm going to do the same to you." Jack said. He pointed to the cornflakes on the table. "Eat up, I'm not letting that go to waste." Jack said. Rainbow Dash picked the cornflakes off the table. "What are these?" Asked Rainbow Dash. "Cornflakes." Jack said. He always put some sugar in with his cornflakes but didn't know if the ponies of Equestria liked sugar that much. Pinkie Pie was his only lead but he thought she over-indulged a little TOO much. Rainbow Dash ate some of the cornflakes. "Ew, it tastes too bland." RD said. "I come from London, of course it tastes bland."

"Have you got any sugar?" RD asked. "Yeah, in the kitchen. It should be on the shelf." Jack replied. RD walked towards the kitchen. It took Jack three seconds before he put down his cornflakes and rushed to the kitchen. RD looked like she was just about to pour the entire thing in. "Hey! I didn't say use ALL of it!" Jack shouted. RD put in an incredibly unhealthy amount of sugar. "It's okay. Having too many of Pinkie Pie's cupcakes really toughens up your stomach." Said RD. She tasted the cornflakes again. "See? Much better!" RD said with a smile. Jack could only laugh, RD may be stupid, but she was nice nonetheless.

"So... have you thought about it yet?" RD asked. "Hm? About what?" Replied Jack. RD rolled her eyes. "About us." She said. Jack had almost completely forgotten about that. "Oh yeah... Uh... I don't know. I'm still scared of upsetting Twilight." Replied Jack, he realized now that there were no humans around, so having a pony girlfriend wouldn't really hinder his social life at all." "But that's the thing. You don't have to tell her!" Said RD. "I don't think that you understand how this works." Said Jack. "Look, just don't tell anyone for a week or something and it'll all be fine!" RD said.

Jack looked at her sternly. "If you say anything about this to anyone it's over, got it?" He said. "So is that a yes?!" RD asked excitedly. Jack sighed. "Yes..." He finally said. "Great!" RD said. Jack got off the couch and picked up his rucksack. "I'm going into Ponyville" He said. "Can I come with you?" RD asked. "Sure, don't say a word about this and it'll all be fine." Jack said. RD moved her hoof across her mouth making a zipper noise. Jack opened the door and was surprised by the weather. He never noticed that it was raining outside, and quite heavily. "Ah, crap." Jack said. the ground was muddy and filled with puddles. "The trees should give us enough shelter from the rain" Jack said. He quickly started running through the forest. "Come on! I'll race you!" Jack shouted. RD was never one to back down from a challenge. She started spreading her wings to glide through the forest.

Jack knew that a Pegasus would probably be faster than him but he wasn't slow himself. He put himself at a pace. Running through the puddles that adorned the ground. RD wasn't far behind. But the branches of the trees were slowing her down and she was going at full speed. Mike almost tripped but managed to regain his balance, the rain made the forest foggy. And it was hard to see the correct way. RD was almost ahead of him. But she looked tired already. Jack knew that only a few more minuted of running would lead him to the edge of the forest. He broke into a full pelt sprint. His speed startled RD at first and she was too tired to go at full speed. Jack jumped over some roots and made a final dash towards the edge of the forest. He stopped immediately when he reached it and realized the rain was heavier than he thought. RD came up to him a few moments later panting. "H-how did you... Go so fast..." RD said in between pants of breath. "I kept a pace. Unlike you. The one thing that bothers me right now is how we're gonna get to Ponyville without getting soaked." Jack said. Ponyville was in draw distance but running there would get his clothes drenched. RD was already flying through the rain to get to Ponyville, unfazed by the rain.

Jack decided to follow and began running through the rain. He instantly felt the coldness of the rain hitting the back of his neck. He continued running for a few minutes until he finally reached Ponyville. He ran for the closest house he knew of; The town library. He ran through the rain to see the familiar looking library and knocked on the door. Twilight answered in a few moments and pulled Jack in. "Oh my gosh Jack! How did you get so wet?" Twilight said. "It's raining outside, bad." Jack said, panting. "I'll go make you a cup of tea." Twilight said. Jack felt his T-shirt. It was soaking wet. he squeezed it gently and a bunch of water came out. _"Crap." _Was the only thing Jack could think of.

Twilight came back with two cups of tea. "...You're soaked." Twilight said. "I'll live." Replied Jack, taking one of the cups of tea. He put his rucksack on the ground, thank god he didn't bring anything important along with him. He and Twilight stayed in the house until the rain stopped around 2 o clock. Jack stepped back out of the library to realize that the streets were still covered in puddles. He decided to go look for RD as they got separated when he came out of the forest.

He walked around Ponyville for a while until he finally found RD sitting on a bench. "Hey! Rainbow Dash!" Jack shouted. RD looked across to Jack. "There you are! I was wondering where you were." Replied RD. Jack took a seat next to her. His clothes still slightly damp. "So where did you go to when we got split up?" Asked Jack. "Oh, I flew to Ponyville and took cover in Fluttershy's house for a few hours." Replied RD. "So... Do you wanna do anything today?" RD asked. "I was probably gonna head back to my house. I don't have anything else to do today." Said Jack. "Alright, I'll come with you." RD said with a smile. The duo went back into the Everfree forest and worked their way back to Jack's house.

Jack opened the door and threw his rucksack next to the wall. "I need to go change." Said Jack. Jack went upstairs and took off his shirt and jeans, he slipped on some new clothes and went back downstairs. RD was sitting on the couch. "Hey Rainbow Dash, can I ask you something?" Said Jack. RD turned to look at him. "Yeah?" She said. "What exactly do you see in me?" Jack asked. This put RD in an odd situation, she liked him for his personality and looks but she didn't want to say that to him. "Um... You're pretty cool. So I decided why not?" She said with a blush. Jack knew she was lying but he went along with it.

Suddenly there was a knock at the door. Jack answered. And was surprised to see princess Celestia standing there. Jack was taken aback. "P-princess?! What are you doing here?" Jack said. "I came here to give you a letter." She said. Jack could make out Luna standing behind her. _"The princess trudged through a forest to get to me? The letter must be important." _Jack thought. Celestia levitated a letter to Jack. "I hope you will be able to attend." Said Celestia, before teleporting away. "Hm... that was a quick encounter." Said Jack. He removed the seal on the letter and began to read it.

_Jack Tailor_

_I, princess Celestia, have decided to invite you and your friends to dinner at the palace tomorrow evening. Me and Luna will be attending as well. I hope you will be able to attend._

_Yours truly_

_Princess Celestia._

Jack was dumbfounded. _"A dinner party? Why? Well, I suppose I have nothing better to do tomorrow._" RD had heard Celestia talking to Jack. "What did Celestia say to you?" RD asked. "She wants me, you and everyone to go to a dinner party tomorrow." Explained Jack. "A dinner party? Sounds boring..." RD answered. Jack only rolled his eyes. It was getting late. "You could stay here again,if you want." Jack offered. "Sure, just as long as I don't have to have that crap in the morning again!" RD exclaimed. "You're sleeping on the couch again." Said Jack as he walked upstairs into his bedroom. RD followed him up. "Oh come on. Do I really have to sleep on that thing again. You have carpet on your floor up here! I could just sleep on that instead!" Said RD. "Fine, sleep on the floor in my room." Said Jack. "Now shoo, I have to change." Said Jack. RD left the room. Jack put on his PJ's and took out his dossier.

_Entry 9_

_So yeah, I'm going out with Rainbow Dash now, Silly right? She seems nice. The princess came to MY front door today and handed me a note saying that there was a dinner party tomorrow and that me and all of my friends could come along. Tomorrow sure sounds like an interesting day. _

_-Jack Tailor._

Jack set down his dossier. He facepalmed. He read the whole thing out loud while he was writing it. Rainbow Dash walked into the room with a blush and a smile on her face. "Don't say anything. Just go to bed." Jack said. RD went to the side of his bed and lied down. Jack laid down on his bed and flicked the light switch of his lamp off.

**Awwww... Isn't that sweet. I should know, I wrote the damn thing. Lol. Anyway, I know nothing really important happened in this chapter and I'm a horrible author. Anyway credit to Redoktober for inspiring me to write this fanfic. I'll probably make the next chapter more intere- Wait, what? 200 VIEWS? LOLWUT? I NEVER EXPECTED TO GET ABOVE TEN!**

**-Cupzy**


	10. The Gift Of Magic

Jack opened his eyes when he heard a noise through the night, he assumed it was nothing and went back to sleep. After morning dawned. He yawned and sat up in his bed. He looked to his left and saw Rainbow Dash sleeping in his bed. _"..." _He nudged Rainbow Dash on the shoulder. She grunted and opened her eyes. "Didn't I tell you not to sleep on the bed?" Jack said. "Yeah, it was pretty cold down there so I decided to come and sleep on your bed. Jack sighed. He felt awkward being this close to Rainbow Dash. "Are you gonna get up?" Jack asked. "I think I'll stay in here a little longer..." Rainbow Dash said. "We have a dinner party to attend tonight. If you aren't awake by the time I finish my breakfast I'm gonna wake you up myself." Jack said. He got out of his bed and put some clothes on. His clothes from yesterday were out of the question. He put on a white T-shirt with grey joggers. He went downstairs and got himself some toast.

He quickly ate the toast as he wanted a good reason to wake Rainbow Dash up. He started thinking about their relationship together and where it would take him. There was no sign of Rainbow Dash once he finished his breakfast so he went back upstairs. Sure enough, she was still asleep. He gave her a nudge to no effect. He then took his alarm clock and set an alarm for two minutes. That should wake her up. He went back downstairs and proceeded to do some cleaning up. When he was finished he heard a loud ringing coming from upstairs which was shortly followed by a scream. He heard RD slowly exit the bed and come downstairs. "Hey! You could have just called my name!" She said. Jack chuckled. "I figured that was a creative way to wake you up." He said.

Rainbow Dash walked towards the door. "Well, I have work today. So I'll see you tonight." Said RD as she closed the door. Jack had no idea what time to go to the castle at. He didn't have anything else to do today. He suddenly remembered back to the letter he read at Twilight's house. It said something about him being able to use magic? Maybe he could spend the day trying to figure out how to use it properly. He had seen ponies like Rarity levitate stuff so maybe he could too. He took a spoon from the kitchen drawer and placed it down on the table. He held out his hand, expecting something to happen. It didn't, he ended up looking like an idiot. He decided to concentrate harder. After a few moments of straining his hand harder and making painful noises. He finally saw a purple glow emanate from his hand.

The spoon itself also had a strange glow about it. Jack moved his hand up and the spoon with it. Cool! He had learned how to levitate things! He took his rucksack and flung it over his shoulder. Maybe Twilight knew more about this magic thing. He traveled through the forest until he saw Ponyville in the distance. Once he had reached the town library, he gave the door a knock and waited for an answer. Twilight eventually answered the door. "Oh, hello Jack! What do you need?" Asked Twilight. "Uh... I was bored in my house and I think I kind of... Levitated something?" Jack said. "You used magic?!" Twilight said. Visibly surprised. "Yeah, I was hoping you could tell me more about it?" He replied. "Of course! I'm one of the most powerful magic users in Equestria!" Twilight boasted. She invited him inside and started to teach him about magic. She showed him how to focus his power to perform more powerful magic. By the end, he had a brief understanding of how magic worked.

"Thanks for the help Twilight!" Jack said. "It's nothing. Just don't use your magic for personal gain or anything, okay?" Twilight said. "Yeah, I won't use it to do anything evil." He replied. He came out of the library. He wanted to find something else to do. But he couldn't think of anything. He just spoke to Twilight. RD was working. So what else could he do? Maybe he could take a premature look at the castle. He started walking towards the cliff side castle that was a ways away from Ponyville.

He managed to eventually reach the castle. He found a pathway leading up the mountain that the castle was located on. He located the entrance and stood looking at the castle. A lot of work was clearly put into it. He obviously couldn't walk straight in. But he just wanted a look at it anyway. The trip had exhausted him. Maybe Twilight could teach him how to teleport or something, could the ponies do that? He had wasted quite some time walking up to the castle. He started walking back the way he came. He Noticed a garden not to far from the castle. He started to walk towards it. On closer inspection, the garden had a bunch of statues in it and a humongous hedge maze was near the garden. He started inspecting the statues. They appeared to be of famous ponies. He eventually got bored of looking at them and turned around to go back to Ponyville.

Back in Ponyville. Jack marveled at his new found powers. He could lift heavy objects with ease which made his life a lot easier. He decided to go find RD, she must have finished work by now. He looked around Ponyville for RD but never found her. When he decided to go back to his house however, he saw her flying around in the sky. "Hey! Rainbow Dash!" shouted Jack. RD saw Jack and landed next to him. "Hey Jack, what do you want?" RD asked. "I was just bored and thought I would come look for you, are you excited for the dinner with the princess tonight?" Asked Jack. "It sounds boring, do I really have to go?" RD said. "Hey Jack?" RD asked. "Yeah? What is it?" Jack replied. "About last night... Did you really mean what you said, about me being nice and all?" RD asked.

"Yeah, I did." Jack answered. "So you really do like me?" She said. "Yeah, you're pretty cool." Jack asked. He looked at Rainbow Dash, she had the familiar "I'm touched." face he saw last night. "Anyway. I should go home and get ready for the dinner." He said. "Yeah... I'll see you later." Said RD. She was obviously embarrassed about Jack admitting his feelings to her. Jack smiled as he went back to his home. He got some nice clothes ready. He assumed everypony would meet up in the middle of Ponyville when the time came. He heard a knock at the door and he went to go answer. Twilight was standing there. "Oh hi Twilight, what brings you here?" Jack asked. "I just came over to see how you were coping with the magic thing." She said. "It's going pretty well." He replied. "Are you excited for the dinner tonight?" Jack asked. "Yeah, haven't been to the castle in ages and I want to talk to the Princess about something.

Jack and Twilight chatted away the night. The time eventually came to meet in the middle of Ponyville. Jack put on some clean clothes and took his rucksack with him, just in case. Him and Twilight walked through the forest until they reached Ponyville, where they saw all of their friends waiting for them. They did the meet and greet and started waiting for some sort of transport to arrive. Eventually several golden chariots arrived to pick everyone up. They got into the carriage and were taken off to the castle. After around an hour they arrived at the large gate at the castle entrance. Everyone but Twilight was admiring the architecture of the castle. When they got off in the courtyards the two princesses were there to greet them. "Hello everyone! I hope you had a nice trip, I would like all of you to follow us to the dinner hall." Princess Celestia said. Everyone followed her into the castle, it consisted of large corridors with rooms at either side, eventually there were a large set of doors at the end of the hallway.

When the doors were opened it revealed an extremely large dining hall. The table that spanned the entirety of the room was spectacular. Everyone took a seat at the far end of the table. With RD and Jack sitting together. After everyone had calmed down, some chefs came around with large plates of food. The food on the plates were a large selection of vegetarian foods, Jack couldn't blame them. They were ponies after all. After the chefs had exited the dining hall, The princess spoke up. "I hope everyone will have a very nice time dining at my castle." She said. Everyone then commenced eating their food. Pinkie Pie was sitting next to Rarity, which, in an honest opinion wasn't a very good idea. Pinkie's table manners were not to Rarity's taste. But she stood strong and tried her best to ignore her.

Everypony was conversing with the pony next to them. Fluttershy and Applejack. Rarity and Pinkie. Celestia, Luna and Twilight. And Jack and RD. All of them talking about separate things. After everyone had finished their meal (well, everyone apart from Pinkie.) the princess once again spoke up. "I hope you had a great time today. The time is late, I implore you all to sleep in one of the spare rooms in the castle. Luxury, of course." Celestia said. Everyone jumped for joy. Celestia leaded them to their room. The room itself was huge. And beds were scattered across the bedroom. Everypony was tired and ready for bed. Apart from Pinkie Pie. Everypony got themselves ready for bed and almost immediately fell asleep on the comfortable beds. Jack just got into a random bed and took out his dossier.

_Entry 10_

_So we went to the castle today, the food was delicious and Celestia offered to keep us for the night. Everpony's (Yeah, that's what everyone says here) already went to bed. I had another talk with Rainbow Dash today. I told her that I really liked her and she seemed pretty happy about it. I'll probably have another talk with her tomorrow. But this time more... in depth._

_-Jack Tailor. _

**So that was the tenth chapter of Anxiety. These fanfics have become easier to write ever since I started to listen to the super Mario RPG forest maze music on a loop. Credit to Redoktober for inspiring me to write this fanfic. Oh yeah and holy crap. over 400 views? In the first week? Wow. Just wow. I expected around 15 or something. I also got my first review and it was a good one! (Even though I know that this story is crap as all hell.) I'm going to make the next chapter strictly about Jack and Rainbow Dash's relationship so I can actually make the story interesting for once.**

**-Cupzy**


	11. Love blossoms

Jack yawned. He looked at his wrist watch. Twelve o clock. Everpony was out of their beds and conversing in the center of the room. Jack got out of bed and grabbed his rucksack. He walked towards his friends. "Oh Jack you're awake! The chariot was just coming to pick us up!" RD exclaimed. Looks like he had good timing. He and the rest of the ponies walked outside of the castle. Within moments the same golden chariots came to them. They all piled into the carriages and made their way towards Ponyville, with Celestia and Luna giving goodbye waves to them as they went. The chariot ride didn't take very long. And soon enough they were back in Ponyville. He and RD got out of the chariots and walked towards each other. "Hey Jack, could I tell you something in private?" RD said, they both walked away from the other ponies.

They reached a small alleyway between some houses. Jack was wondering what RD wanted to tell him. Just as he was about to open his mouth to speak to her. RD turned around and pulled Jack in, kissing him. Jack didn't retaliate, rather he enjoyed every minute of it. RD pulled away after a few seconds and looked at Jack with a smile on her face. "I really like you Jack." Said RD. "Yeah, I like you too." Jack replied with a smile on his face. Jack wasn't lying, he really did like RD. He wouldn't go as far as to say he loved her though... Yet. Jack eventually spoke up. "I'm gonna make this less awkward and say I'm gonna go home now." Jack said. He wasn't really going back to his house. He just wanted to think about him and RD. He knew that she loved him, and if he was asked, he would probably say the same too.

Jack took a few steps out of the alleyway and then realized. Could Twilight teach him something about teleportation? He went towards Twilight's house and knocked on the door. When Twilight answered. Jack was the first one to speak up. "Hey Twilight. I want to ask you something about the whole magic deal." Jack said. "Sure! What do you want to know?" Twilight replied. "Could I be shown how to teleport?" Jack asked. Twilight gulped. "Yes, but that requires more magical power than I have." Twilight said. "I'll give it a go." Said Jack. Twilight showed Jack some dusty old magic tomes. He learned the basics of teleportation and decided to give it a go. He stood in the middle of the library. He stressed his mind thinking of a place he wanted to go to and snapped his fingers for vanity. He felt a strange magical force around him.

He felt a completely different air about him when he opened his eyes. He was in a different place for sure, but where? Everything was white. Suddenly he heard a noise coming from a door next to him. He opened the door which startled both him and a confused Rainbow Dash. They both jumped back. This was the place he wanted to go but he never expected it to work! "AH! Jack? What the heck are you doing here?" Said RD. "I was testing out a teleportation spell with Twilight and um... It worked." Jack said. "Wow, you can teleport? I thought only the princesses could do that..." RD said. _"Only the two of them? It was pretty easy!" _Jack thought to himself, dumbfounded. "Well, since I'm here is there anything you need help with?" Jack asked. "Nah, not really. Maybe you should just head back." RD said. Jack nodded and readied up the teleportation spell again. He could do it quicker this time, he snapped his fingers and was back in Twilight's house. "Wow! You did it Jack!" Twilight said. Jack couldn't hear her, he could only hear ringing in his ears. He felt a heavy pain in his head and closed his eyes.

Jack awoke with a jolt. Twilight sparkle and the rest of the ponies were sitting around him. "Hey! He's awake!." Twilight shouted to her friends. RD looked relieved. Jack's head was still hurting. "Ah... God, what happened?" Jack asked. "You used too much magic, you managed to knock yourself out. Be happy you're still alive! Two teleportation spells could easily kill anypony!" Twilight said. "The only person able to pull that off was princess Celestia, and even she was unconscious for two days!" She continued. "How long have I been out?" Jack asked. "A day." Twilight responded. "NEVER do that again." RD exclaimed. "You were scaring me!" She continued. "It's alright, I feel fine." He replied. "You'd better stay in bed for another day. We don't know what kind of side effects this could bring." Twilight said.

Jack spent the rest of the day in bed. He was constantly visited by both Twilight and RD. Twilight came around every hour or so to see if he was feeling okay. Rainbow Dash was sitting outside of his room, worried sick about him. This was the first time he'd seen RD so depressed. Meanwhile, outside of Jack's room. Twilight and Rainbow Dash were sharing a conversation. "Why are you sitting outside his room? You haven't had anything to eat, drink and you can't sit around all day. Why are you so worried about Jack?" Twilight asked RD. "I dunno, he's a good friend and I'm worried about him, you got something wrong with that?" RD replied. She remembered the promise that she made to Jack to not tell anyone about their relationship until later on. "But you aren't acting like yourself, normally you would visit once and then go." Twilight said.

"Yeah, well me and Jack hang around together a lot and he's become a really good friend." Rainbow Dash said, lying through her teeth. Twilight was starting to have her suspicions. "By the way Rainbow, can I tell you something personal?" Twilight asked. "Sure, shoot." Replied RD. "Well, I used to go out with Jack, just for a day or two to see what it was like. I got really attached to him but he broke up with me a few days in. Do you think he hates me?" Twilight asked. "Well... uh... I'm sure he doesn't HATE you, he's still a really good friend to you right? Maybe he just wanted some... Free time?" RD said resisting the urge to punch Twilight in the face. "Okay. Thanks Rainbow Dash, you've been a great help." Said Twilight. "No problem Twi, but I'll probably stay around, you know, just in case something urgent happens." Replied RD.

Jack was getting bored. Suddenly, Twilight walked into his room. "Hi, Twilight." Jack said. "Hi Jack. I brought you some food." Twilight said. "Thanks, I appreciate it." Jack said. This coaxed a smile out of Twilight. She knew he didn't hate her, she was just experiencing angst or some other soppy crap. She left him to eat his food. After a few more hours Jack felt perfectly fine. He could stand up without any hesitation. He looked a his wrist watch, 7 o clock at night. He walked out of his room to see RD about to doze off at the side of his door. "Hey Rainbow Dash. When did you get here?" Jack asked. "I've been sitting here for the past six hours..." RD explained. "Oh, I never knew you were that worried about me..." Jack said. He walked downstairs. He saw Twilight. "Hey Twilight." Jack said as he sat down net to her. "Oh You're up. Are you feeling alright?" Twilight asked. "Yeah I'm fine, I won't do the same thing again." Jack replied.

"I'm probably gonna go take a walk." Jack said before getting up and leaving the library. A few ponies still lingered on the roads. The street lights were on. It looked almost as dull as London. He yawned and started walking towards his house. He wasn't exactly fit for running home in this state. After around an hour he finally managed to find his house in the pitch-black forest. He entered his house and threw himself on the couch, using magic sure takes it all out of you. He assumed everypony was in bed and sleeping happily, he was stuck on his couch exhausted. He heard a knock at the door, he mustered all of his strength to lift himself off his couch and answer the door. It was RD. "Hey Jack, I was just wondering if you were alright." She said. "Fit as a... fiddle." Jack said in between pants of breath. "Can I stay here tonight?" RD asked. "What, do you live here now?" Jack asked.

"I suppose, I mean I like your house. And I'm not gonna be the one waking you up every morning!" RD said. "Believe me, I'll always be awake before you." Jack said. This got a laugh out of them both. "Well, I'm tired, I'm gonna go to bed, you can stay up if you want but don't break anything." Jack said. He walked upstairs into his bedroom, it took a full 10 minutes to get his PJ's on, he was so exhausted. He slumped onto his bed and lazily took out his dossier.

_Entry 11_

_I'm fucking tired, I learned how to use magic and I tried teleporting (sounds crazy I know.) and I ended up exhausted because of it. RD decided she's gonna stay at my house from here on out. She actually kissed me today (I know, kissing a horse.) But it just felt... Natural. I don't think there's anything wrong with this anymore. I'm really starting to like RD. Anyway, I'm too tired to write anymore._

_-Jack Tailor._

__**Awwwww... Dey kissed :3 Anyway. I know this chapters pretty short but some urgent stuff came up today I had to take care of (Involving my dog and a speeding car) and that kinda hindered me from writing this chapter. Once again credit to Redoktober for giving me the inspiration to write this fanfic. I will make this story less crappy soon. Just wait for it. **

**-Cupzy**


	12. The rematch

Jack yawned. He didn't want to get up today. He looked at his alarm clock. 10 o clock. He felt much better than yesterday. His instincts triggered and he pushed the opposite end of the bed, knocking RD out of it. "Good morning." Jack said, looking at her with a smile. "Very funny." RD said as she walked out of Jack's room. Jack got up. He felt revitalized after what happened yesterday. He yawned and proceeded downstairs. Rainbow Dash was sitting on the couch. "Morning darling." Jack said with a chuckle. "Don't start calling me soppy names." RD said with a smile. He went to the kitchen and made himself two plates of toast. He levitated one plate in front of Rainbow Dash. "What's that?" RD asked. "It's essentially bread warmed up." Replied Jack. RD took a bite. It wasn't as bad as she expected it to be. Jack sat down next to Rainbow Dash.

"Hey Jack, what happens when you run out of food?" RD asked. He hadn't thought of that. "I'll get a job probably, then I'll have to live off vegetarian meals." Jack said. He couldn't remember the last time he ate meat. "Hey! You could come work with me!" RD said. "I don't have wings." Jack said. "Yeah but you can teleport." RD said. "Remember what happened last time I teleported? It didn't turn out so well." Explained Jack. "Besides, I've probably got enough food to last me a few more weeks." He continued. "Well, I've got the day off today so I could just hang around with you most of the day." RD said. "You're really attached to me." Jack said. "Well, you're a cool guy. Plus we are kinda... you know." RD said. "Yeah." Jack replied.

"I'm gonna head into Ponyville. I'm probably gonna try teleporting there." Jack said. RD had a worried look in her eyes. "You sure that's a good idea?" She asked. "I got knocked unconscious when I used it twice. I should be fine." Jack said. He snapped his fingers and there he was, in the middle on Ponyville. This teleportation thing was gonna come in handy. He was gonna leave quite a gap of time between teleports so that he wouldn't be knocked unconscious again. He walked towards Twilight's house. _"Maybe it's about time I told her about me and RD. The faster I get it over with, the better." _Jack thought to himself. He eventually reached Twilight's house and knocked on the door. Spike answered. "Hi Jack, you wanna come inside? He asked. "Yeah, I've got to tell Twilight something." He said as he walked inside. He saw Twilight studying between some bookcases.

"Hey Twi." Jack said. She turned around. "Oh hi Jack, what are you doing here?" Twilight asked. "I've... uh... Got to tell you something..." Jack stuttered. "Hm? what is it?" Twilight said, intrigued. Jack sat down next to her. "Well... I've uh... found someone else..." Jack explained. "Wow, that was fast! Who is it?" Twilight asked. She didn't seem terribly angry at this point. "It's uh... R-Rainbow Dash..." Jack said. "You're going out with Rainbow Dash? That's great! I'm happy for you!" Twilight said with a smile on her face. She didn't look that affected. Which wasn't a bad thing. "So have you two... like..." Twilight trailed off before she got ahead of herself. "N-no! I don't intend for that to happen!" Jack flustered, blushing. Twilight giggled. "Well, I'm sure you two lovebirds have something you wanted to do today." Twilight said, still smiling. "Uh... Yeah. I'll be going now." Jack said. he walked out of the library.

She took that surprisingly well. She didn't seem flustered at all. That was a load off of Jack's back. He decided to go look for RD. He spent a little bit of time looking around Ponyville before a cyan object passed him at an incredibly high speed. It came to a halt after turning around. "Hey Jack! I was just looking for you!" RD said. "Really? What do you want?" Jack replied. "I want a rematch!" RD demanded. "A rematch? What for- Oh, you mean a race, right?" Jack said. "Yup." Jack never backed down from a challenge. "Alright, you're on." Jack said with a grin. "Ok, the race will consist of one full lap around the outskirts of Ponyville. The first one back here wins." RD explained. The two took a starting position outside of Ponyville."3... 2... 1... GO!" Shouted RD. She took off. But this time she took a pace. Jack did the same.

They were moving at almost the exact same speed. The race track was longer this time and RD had the advantage considering she didn't have any obstacles to dodge. Jack noticed a gathering of ponies from Ponyville watching them and cheering them on. When a sharp turn came along, Jack angled himself so that he wouldn't lose much speed. RD was adjusting her wings to the sharp turn. The two of them lost speed when making the turn but managed to recover after a few seconds. Jack had started breathing heavily. He assumed RD was in the same state, when half of the race track was behind them, Jack started to pick up speed. He eventually broke into a full pelt sprint when most of the race track was done and the finish line was in sight. RD and Jack were both extremely close to finishing. Almost every single pony in Ponyville had come outside of their homes to watch the duo race. Jack summoned the last bit of energy he had and leaped for the finish line. RD was straining her hoof to reach it. Jack fell on his face, he was in an unbearable amount of pain while he was panting for breath. RD was lying next to him doing the exact same thing.

Ponies started to gather around the aching bodies of the two. Jack could hear them talking. "That was incredible!" "I've never seen somepony move so fast!" Jack got up after he had got his breath back and looked to RD. "We'll call it a draw, okay?" Jack said. "Y-yeah..." RD said, still panting for breath. He was helped up by some ponies. "I'll probably head home now." Jack said. "I'll see you there Rainbow." Jack said. "Okay... Let me just... Catch my breath..." RD replied. Jack snapped his fingers and disappeared. He reappeared in his house. He sat down on the couch. _"Damn, she moves fast... I'm never doing that ever again." _Jack thought to himself. He went upstairs to take a nap.

He yawned and looked at the clock. 8 o clock. He had slept for longer than he wanted. He got up and heard some noise from downstairs. RD was probably home. He went downstairs and saw Rainbow Dash inspecting a TV remote thinking it was some kind of alien object. "Hello." Jack said. "Oh there you are! I was wondering where you were." RD said. "I'm tired, I think I'll go to sleep." RD said before lying down on the couch. Eventually Jack spoke up. "*Sigh* You can sleep in my bed if you really want t-" Jack was interrupted by the sound of RD walking upstairs. He decided to follow her. He found her laying limbless on the bed, fast asleep. He put on his PJ's, went into the opposite side of the bed and took out his dossier.

_Entry 12_

_So I told Twilight about me and Rainbow Dash today, she took it better than I was expecting, so that was a huge weight off of my shoulders. Me and Rainbow Dash had another race today, we called it a draw and by the end we were almost dead. Rainbow Dash now officially lives at my place and she sleeps in my bed. Although I still really like her. She's sweet in her own way._

_-Jack Tailor._

"So that's your second name!" RD said from the opposite end of the bed. She was sitting next to him. Looking at his dossier. "Do you really think I'm sweet?" RD said with a smile. "Yeah, you are." Jack said, smiling back. RD blushed as she turned out the light.

**So I made this chapter a little late today simply because I was catching up with my old friend Jack (Not the one from the story) And yeah, I made this a little late. Today I had to confess to my best friend that I was a brony, needless to say he took it pretty well, His reaction was essentially my inspiration for the Twilight part. He doesn't know I write fanfics yet so... Speaking of inspiration, Redoktober's a good guy, maybe you should check him out or something, he makes some kick ass fanfics. Peace.**

**-Cupzy**


	13. The Mysterious Pony

**I have now officially decided that _Wednesday will now be my day off from writing these _but I'll probably upload the fanfic on Thursday earlier to ****compensate.**

Something poked Jack when he got up.

"Hey! Why do you sleep so much?" He could hear Rainbow Dash calling to him.

He looked at his alarm clock, 8 O CLOCK?!.

"Crazy bitch! You wake me up at eight and tell me I'm lazy?" Jack said angrily.

Jack sighed and got up. He was never going back to sleep now. He walked downstairs and made himself some toast. Shortly after finishing the toast, he heard RD coming downstairs. "You call me lazy and sleep in longer than me?!" Jack shouted. "Man, you're cranky in the morning." RD said. Jack sighed, he liked her but reasoning with her was a completely different story. She sat down on the sofa next to Jack.

"So... About yesterday..." RD said.

"There's nothing wrong with it. I let you into my bed, simple as that." Jack said as he stood up.

"I'm heading into Ponyville." Jack said.

Just as he was about to snap his fingers, RD grabbed his sleeve.

"Hey, at least give me a kiss before you go." RD said with a smile. Jack knelt down and moved himself towards RD, he closed his eyes and his lips were soon met with RD's. She certainly made it last. She pulled away after a few seconds. Jack smiled, just as he snapped his fingers he heard three words.

"I love you." Were the only words Jack could hear. He smiled to himself, if he had the time, he would have said the same back. There he was in Ponyville. He noticed a large commotion coming from the town square. He saw ponies circled around something. He moved his way to the center of the crowd until he could see what was going on. A pony was lying down on the ground. It was bleeding quite bad. There was commotion going on around the crowd. Some asking who the pony was, some asking where it came from.

Whoever it was, it was hurt, badly. Jack walked to it to inspect it further, it had bruises all over it's body, the worst parts bleeding. It looked like she had fallen from the sky, there were cracks all over the ground near it, indicating some sort of impact. What could he do? Could he heal the pony with magic? No, he didn't know how to do that, it was worth a shot though. He placed his hand on the pony's chest. He focused all of his magical power and wondered what to do. He just thought about bandages and other medical stuff. Suddenly a green glow emanated from his hand. He wasn't sure what he was doing but it was certainly working. The pony's wounds were closing! After tending to the open wounds, he had stopped the bleeding. The green glow faded from his hand. He could barely stand up, he was so exhausted.

Some of the ponies standing around the body started to mumble. He could hear questions about who he was, more importantly, he could hear people asking WHAT he was. He spotted his friends standing in the crowd. Looking at him in disbelief. RD was there as well. Jack managed to stand up. But he could barely keep like that. His legs were shaking and he didn't feel too well. After a few moments. He could stand up properly again. He looked back at the injured pony. It had regained consciousness and was attempting to stand up. It was breathing heavily.

"Someone get her to a hospital, my magic only did so much." Jack said. He walked over to his friends.

"Jack, that was amazing!" Rarity exclaimed. He could hear all of his friends complimenting him, especially RD.

"Let's all head back to the library." Twilight said. Everyone agreed. They all walked back to the town library. Jack could hear Applejack and Fluttershy talking about Jack's exploits. Once they had finally reached the town library, Jack felt fine again. They all sat down at separate tables. Twilight and Rainbow Dash sat with Jack.

"Jack, when did you learn to use a healing spell?" Twilight asked.

"I don't know, It just kinda... happened." Jack explained.

"Man Jack that was AWESOME! You saved somepony's life!" RD shouted.

"I think we might need to see the princesses about this... Your magic capabilities far exceed my own." Twilight said, slightly disappointed.

"I agree. I want to find out how much more I can do!" Jack said. He now realized that he could do great things with this magic. He got up.

"I'd better start going back home. I don't want the entirety of Ponyville chanting my name" Jack joked.

"I'll go back with you." Said RD. They walked out of the library and began walking home. RD had an odd look on her face, it was a mix between excitement yet fear. What was that called again... Oh yeah! Anxiety. It probably had something to do with what she said earlier today, Jack supposed that she was afraid that he would take it the wrong way, but still excited over what the outcome would be.

"I suppose you wanna talk about this morning?" Jack asked.

"W-why? I can't remember anything happening this morning..." RD said, lying.

"I heard you loud and clear. I just wanna say that I feel likewise." Jack said. RD stayed quiet. Her regular tomboyish personality was completely gone now.

"R-really?..." RD asked. Her face was literally as red as a rose.

"Of course. I've known you for long enough to tell you that _I love you._" Jack said. _I love you._ The three words that RD was trying to coax out of Jack, she smiled at him and got one back. They were happy together. They eventually reached Jack's home.

"I hope it can go without saying that you can sleep in my bed tonight." Jack said with a smile.

"Yeah, thanks." RD said. Smiling back. She went upstairs, shortly followed by Jack. She was already asleep, probably tired by today's events. Jack put on his PJ's and took out his dossier.

_Entry 13_

_So some kind of weird pony fell from the sky today, that's when I learned I had healing magic, cool huh? Anyway. Me and Dashie (That's what I'm calling her now.) Finally talked about each other. We both said that we love each other. Living in Ponyville is actually a really cool experience. I'm starting to like it more than London! Me and RD really are happy with each other. I hope it keeps that way.  
_

_-Jack Tailor._

**SMALL/CRAPPY CHAPTER APPROACHING, BRACE FOR IMPACT. Anyway, that was a short chapter, if you've read every chapter before this then you might be thinking to yourself: ZOMG, CUPZY'S ACTUALLY WRITING LIKE A NORMAL PERSON NOW, OMG HE MAY NOT BE SO BAD AT THIS AFTER ALL. Yeah, apart from the last part, I made that up. I got a review the other day that actually had constructive criticism in it. I took the liberty of listening to it and realized that I'm worse at this than I thought. So by listening to this guy I've made this fanfic around 0.01% better. Once again credit to Redoktober for inspiring me to write this fanfic. Check him out, he's pretty cool. (Credit to the review dude as well, he helped.) Peace.**

**-Cupzy**


	14. The Duel

Jack opened his eyes to see Rainbow Dash on the opposite side of the bed. He smiled and got up. He went downstairs as quietly as possible so as not to wake RD. Once he was downstairs he made himself a bowl of cereal. He sat down on his couch and wondered what he was going to do today. Suddenly, he heard a knock at the door. He set his cereal down on the table and walked to the door. Standing there was a small brown Pegasus.

"Hello, you must be Jack, correct?" The pony asked.

"Yes, that's me. Who are you?" Jack asked.

"My name is Celine, I wanted to thank you for saving my life yesterday." Celine said, Jack suddenly remembered yesterday, he never expected the pony to be out of hospital in one day.

"Ah, that was you. I never expected you to be out of hospital so quickly." Jack said.

"The more serious injuries were treated by you. If it wasn't for you I wouldn't be here right now." Celine said. Jack noticed that Celine had stitches around her body, mostly near her cutie mark. Which depicted three Z's. (I'm unoriginal, shut up.)

"I run the hotel in Cloudsdale. I was flying to Ponyville to catch up with a friend when a rude Pegasus came rushing past me. He collided straight into me. I was sent spiraling down to Ponyville. I was knocked unconscious when I hit the ground." Celine explained.

"I see. How did you find my house?" Jack asked.

"Ah, your friend Twilight Sparkle tipped me off about your whereabouts." Celine replied. Jack motioned for her to come in. She sat down on the couch.

"Do you want a cup of tea or anything?" Jack asked.

"If it wouldn't bother you." Replied Celine. Jack continued to make three cups of tea. In case RD woke up in the middle of it. Sure enough, he heard her lumbering downstairs a few minutes later.

"What's with all the noise?" RD asked.

"The pony that I helped yesterday came over to say thank you." Jack said.

"Hm?" RD said as she looked over to the couch, where she saw Celine.

"Oh, right."RD said.

She walked over to Celine, the two started to chat. Jack poured the tea into the cups and brought them through, placing them on the table. He took a seat on the remaining space on the couch.

"-So he must have been in quite a rush." Celine said.

"Man, what an idiot. Some ponies just don't care for each other." RD said. Celine looked at the clock in the living room.

"Oh, look at the time. I really must be going." Said Celine. She got off the couch and exited the house.

"Anyway... Morning Dashie." Said Jack.

"Yeah, good morning." Jack said. Suddenly, a knock at the door was heard again.

"Damnit! We can never get any peace around here!" Jack exclaimed as he opened the door. He looked down and saw Spike, panting.

"Oh hey Spike. What's up?" Jack asked.

"L-letter... From princess... Celestia." Spike said in between pants. His cheeks filled up with air and he shot a green flame out of his mouth, turning into a scroll. Jack caught the scroll and began to read it.

_Dear Jack._

_I hope this letter finds you well, my student Twilight Sparkle tells me that you display incredible magic prowess. I would very much like you to come over to the castle tonight so that we may talk about the situation. _

_Yours truly, Princess Celestia._

"Thanks for the information Spike." Jack said as he handed the scroll back.

"No problem Jack." Spike replied as he turned around and started walking back to Ponyville.

"What was that all about?" RD asked.

"Princess Celestia wants to see me tonight to discuss my powers." Jack said.

"I'm going to head into Ponyville." He continued.

"Hey Jack? You know that teleport-y thing you do?" RD asked.

"Yeah, what about it?"

"If I held on to you, would you take me with you as well?" She asked. Jack wasn't sure if that would work.

"It's worth a try, I suppose." Jack said. Rainbow Dash grabbed Jack's trousers. He snapped his fingers and was in Ponyville. Sure enough, RD came with him.

"You feeling okay?" Jack asked.

"A little dizzy, but I'm alright." RD replied. They continued to walk to the castle.

"Although she said "Tonight" I'm sure she won't mind if I turn up early." Jack said. The two started walking towards the castle. Along the way they had a talk.

"Why do you think she's so interested in me? Isn't she the most powerful pony in all of Equestria?" Jack asked.

"Yeah, but she took a few hundred years to learn all of her magic abilities." RD replied.

"A few hundred years?!" Jack exclaimed.

"The princesses are immortal, didn't you know that?" RD said. Jack shook his head. After a few more hours of walking, they finally reached the castle. They walked up to the two guards that were guarding the gate. They opened the gates for Jack and RD to go through. Jack had been here before but he didn't remember the exact layout.

"Have you no idea where to go?" A voice said from behind Jack. He jumped forward and looked back. Princess Celestia was standing there. She let out a small laugh.

_"I've never seen a princess that openly greets her visitors by frightening them..." _Jack thought to himself.

"I thank you for coming Jack. What we are about to talk about is of no laughing matter." Celestia said.

"It was no problem. I wasn't going to be doing anything today anyway." Jack said.

"Please do follow me." Asked Celestia.

They walked through the corridors of the castle. It looked much smaller from the outside. They were eventually led to a large throne room. The architecture was amazing, there were stained glass windows of the history of Equestria, even one depicting Twilight and her friends.

"Jack, I have brought you here to talk about your magical prowess. Please take a seat." Celestia said. Jack pulled up a seat from the corner of the room.

"As you may know, me and Luna have the largest magical power in Equestria, Twilight also displays large magical ability. But you seem to have an unlimited amount of magical capability. You can learn spells simply when put in the correct situation. Now, Jack. What I am about to ask you may hinder you a little."

"Yes Princess?" Jack said, expecting some kind of reading task.

"Would you... Care to have a magical duel with me?" Celestia asked. Jack was taken aback, a princess just asked him to DUEL.

"B-but princess, you and I know that I would probably lose straight away. Plus the addition of either of us being hurt-" Jack was cut off by Celestia.

"We will abide by strict dueling rules, we will each have a magical shield over each other. Every offensive spell that lands on either of us will take away the shields power. In layman's terms, three hits and you lose." Celestia explained.

"The point still stands. You're the most powerful pony in Equestria." Jack said.

"Yes, but I believe that you do not know the extent of the power that you can achieve." Explained Celestia.

"What about the area we should duel in?" Jack asked.

"There is an open part in the forest that we may duel in. The clearing holds no wildlife and is perfectly safe." Celestia explained once more.

"...Alright, I'll give it a go." Jack said.

"Spectacular!" Celestia said. Suddenly the three of them were teleported to a large clearing in the forest. RD sat on a rock away from the duel area. Celestia's horn glowed and he could feel a transparent force around him.

"Are you ready to begin the duel, Jack?" Celestia asked.

"As willing as I'll ever be..." Jack said.

"Then the duel shall commence!" Celestia shouted. It was silent for a minute. Jack was smart and decided to wait for Celestia's first move. After a few seconds her horn glowed and a large blue projectile came rushing towards Jack, he jumped out of the way just in time. His heart was racing. Jack had no idea what to do. He didn't know any fighting spells. A seconds projectile came right at Jack, hitting him in the chest. He was sent back towards a cliff face.

_"Damn... Even with the shield on, that one still hurt." _Jack thought to himself. He barely had any time to think before another projectile came towards him. He held up his hands in retaliation. Instead of being knocked back. He didn't feel the projectile at all. He opened his eyes and realized that he had managed to stop it. He must have conjured up some sort of shield. Jack ran to one of the bushes nearby. Hiding. He heard hooves coming into the clearing a few seconds later.

"Has he lost already?" Celestia said to herself. Jack held up his hand. All it took was a little bit of imagination, right? He focused until his hand was a dark red color. He poked his head above the bush and threw his hand forward. He shot some sort of red projectile at Celestia. She was caught by surprise and was hit in the chest by the projectile. She was knocked back. She made a loud "Oof!" When she landed, surprised that Jack managed to hit her that hard. She got back up. She saw Jack's head poking put from the bush.

"You rely on stealth to win all of your battles? Or are you just afraid?" Celestia shouted in a very un-princess like manner

_"A princess who taunts her opponents. She's almost as bad as Dashie when she gets determined..." _Jack thought to himself. A small beam came towards Jack's bush, he jumped out just before the bush was annihilated. Jack started running around randomly. He threw another projectile at Celestia. Which she quickly dodged. She continued throwing projectiles at Jack until he finally tripped over. Celestia was about to use the beam move again. He quickly got up to his feet but was too slow. Celestia managed to hit his leg with the beam. Counting as a hit. He was down to his last chance. And Celestia had only been hit once. Jack stopped and instantly ran towards Celestia, before she could react. He threw another projectile straight at her. It was going too fast for her to dodge. She was once again sent back. They were now both on their last chance.

"You have fought well Jack, but I think now is the time to end this." Celestia said. Her horn started glowing. From her horn, a massive purple ball was created. She shot it from her horn at almost the speed that RD flew. He quickly ducked and the ball went soaring passed his head. The cliff face that he previously was thrown into was now completely destroyed. Celestia obviously used a lot of magic for that. Her legs were shaking and she didn't look very well. Jack took the opportunity to throw one last projectile. It hit Celestia square in the face and sent her flying. She hit the bark of a tree. She fell down after a few seconds. Both her and Jack were panting.

"You beat me fair and square..." Celestia said. Jack outstretched an arm

"Yeah, but you would've gotten me if you had hit me with that last attack." Jack said.

"It seems you surpass even me with your magic." Celestia said.

"I never intend to do anything bad with it. I can tell you that." Jack replied. Celestia smiled and teleported them back to the castle. She was exhausted.

"I am going to go rest. You should too." Celestia said. Jack nodded and teleported him and RD back to his house.

"Wow Jack that was AWESOME! You beat the princess in a magical duel!" RD exclaimed.

"Either way, I'm tired, I'm heading to bed." Jack said. He walked upstairs, put on his PJ's and took out his dossier

_Entry 14_

_So I kind of fought a princess today, I'm not wanted or anything but I won so I'm kind of the most powerful thing in Equestria now. I don't really care I mean it's not like I'm gonna use it for anything other than helping people out. The pony from yesterday also came along and said thanks._

_-Jack Tailor._

**SO YEAH, TOTALLY UNRELATED CHAPTER TO WHAT THE STORY'S SUPPOSED TO BE ABOUT. I AM A GREAT FANFIC WRITER AREN'T I... WHO AM I TALKING TO? Anyway so yeah, I'll probably make the next chapter focused on the JackxRainbowDash thing. I'm also trying to make up for the SMALL AND SHITTY CHAPTER I MADE YESTERDAY. So yeah... Credit to Redoktober for inspiring me to write this fanfic. Peace.**

**-Cupzy**


	15. The Ursa Major

Jack woke up, yesterday was a busy day. He felt some kind of warmth next to him. He moved his hand over to his right side and felt hair. He opened his eyes and looked to his right, Rainbow Dash was snuggling up next to him. Jack sighed. He gave her a tap on the head. He heard some grumbling and finally some movement was registered. He heard a loud yawn. He could tell that she had opened her eyes. He could almost feel the heat coming from her blush. She backed away from him to her side of the bed.

"It's pretty funny actually, I planned to make some rules of _what we shouldn't be doing in bed_ when we were in the bed last night, I must have forgot." Jack said calmly. Rainbow still had a humongous blush on her face. She was speechless.

"U-uh... I... It was... Pretty cold last night and you looked really warm so I kinda... uh..." Rainbow eventually said, lying through her teeth. Jack laughed.

"No need to explain, I never knew you were that attached Dashie." Jack said. She was still pretty speechless. Jack got out of the bed.

"That aside. I think we should probably get up." Jack said. Rainbow nodded. She got out of bed. Her face still bright as a cherry.

"Uh... Y-yeah, agreed." Rainbow said. They both went downstairs. Rainbow waking up at the exact same time as him was a rare sight. He continued to make two bowls of cereal. He tried Shreddies. Who doesn't like Shreddies? Well, Rainbow, apparently. She almost spat them out after eating them.

"Ew... How can humans eat this? It's too... Bland." Rainbow said.

"I think they're pretty tasty. I can't talk I suppose. Everything in Equestria tastes like a bowl of sugar anyway. Even the salads!" Jack said. After Rainbow reluctantly finished her cereal. Jack spoke up.

"Hey Dash? You don't think that princess Celestia... Told anyone about yesterday do you?" Jack said.

"Probably Twilight and no one else. Although most of the gossipers in Ponyville have guards for husbands, and I bet they probably heard the commotion from the forest." Rainbow said.

"Great. Nobody listens to gossipers." Jack said reassuringly.

"You wanna come with me to Ponyville?" Jack asked.

"Sure, I got nothing to do today anyway." Rainbow grabbed onto Jack's trouser leg and he snapped his fingers. He had some weird looks from the residents. They were surprised first time to see a human in Equestria but they had gotten used to it.

"I suppose people DO listen to gossipers..." Jack said. He had extremely strange looks from the residents, some of them were mad, some were cheering him on. He eventually reached the town library. He knocked on the door. Twilight answered.

"Jack! What are you doing wandering about?! Get in here!" Twilight said. Jack and Rainbow entered the library.

"Why the attitude Twi?" Jack asked.

"Everyone in Equestria knows about what you did yesterday!" Twilight shouted at him. This surprised Jack.

"Why? I guessed that she would have told you, but why everyone?" Jack asked.

"I'm not too sure." Said Twilight. Rainbow took a seat on a chair.

"You'd better keep a low profile until this commotion simmers down. Why aren't you surprised?! You've now been declared the strongest entity in Equestria!"

"She DECLARED that to everyone?!" Jack said. Now visibly shaken.

"Yes! And being the strongest thing in Equestria. Everyone has a right to fear you!" Twilight said.

"That's alright, all I have to do is lay low, which is perfectly fine." Jack said calmly. Twilight sighed. Not only was she stressed about one of her friends being dangerous, she was now revoked of her status of being the third most powerful entity in Equestria!

"Well, I'm probably gonna head into Ponyville to get some food and stuff. I'll be back later alright?" Jack said. The two ponies nodded.

"Jack, be careful out there..." Rainbow said. Jack chuckled.

"It's not like anyone's going to hire pony-assassins to kill me. I'll be fine." He said as he closed the door.

(Initiate changey-perspective thing)

"I really hope he comes back safe." Rainbow said.

"He'll probably be fine. He'll get hated on by the residence but they won't do anything drastic... Hopefully. Oh, Jack tells me that you two are going out now?" Twilight asked.

"Yeah, me and him have been going out for about a week now. We're pretty happy with each other." Rainbow said with a smile.

"That's nice. How did you know about Jack and Celestia?" Twilight asked.

"Oh, I was there." Rainbow answered.

"You were THERE!? Weren't you hurt?" Twilight asked.

"Nah, I just stayed far away from them." Rainbow responded.

"Why were you there?" Twilight asked.

"Jack dragged me along." Rainbow replied.

"I see. Has he actually told you that he loves you?" Twilight asked.

"Once, he seems pretty embarrassed about it, although I can't really say anything. I've gotten myself into more awkward situation than he has." Rainbow replied. The door swung open, Jack was standing there with some grocery bags.

"Well I'm done. The ponies didn't take too kindly to me walking outside. They seemed pretty afraid of me. I'm probably gonna head home and lay low for a while." Jack said.

"I'll go with you." Said Rainbow. Jack snapped his fingers and they were back at his house. He set the groceries down on the kitchen table.

"How long do you have to lay low for?" Rainbow asked.

"I'm probably gonna give them a day. Then I'll go back to Ponyville." Jack replied.

"I guess Ill just stay in with you then." Rainbow said. Jack smiled at her.

"So... uh... About this morning..." Rainbow said. Jack looked at her.

"What of it?" Jack replied. Rainbow shook her head, she was going to lose her reputation if she went all mushy on Jack.

"I just... Uh... W-what I said was the truth, no doubt about it." Rainbow said as a way to escape the conversation she herself had started. Jack knelt down next to her.

"You don't have to lie. I understand." Said Jack.

"Y-you do?" Rainbow said with a confused look on her face. Jack let out a small chuckle.

"Of course I understand. I'm your boyfriend after all." Jack said. This made Rainbow Dash blush. She pulled Jack forward into a kiss. She really did love him. She made it last this time. She eventually pulled away. She shook her head with a violent blush and ran upstairs. Embarrassed.

_"Poor, egotistical Rainbow Dash." _Jack thought to himself as he shook his head. He decided to go outside. Despite having lived her for over two weeks. He never got a proper layout of the forest area around him. Only the part towards Ponyville. He started to walk in a direction he hadn't walked before. The forest seemed to look the same no matter where you were. He sighed. He had spent around an hour walking around the forest. He sighed and turned around. He saw something in the distance. He went into a bush to observe the creature. It was huge. It had purple skin that looked like the night sky. It resembled a bear. It suddenly looked in Jack's direction, spotting him.

Jack just sat there, eyes wide open. The creature eventually started running towards Jack, he turned around and started to run, whatever it was. It was mean. He ran back in the direction of the house, following the small breadcrumbs he had left for himself. After finally reaching his house. He realized that big ugly bear monster plus house was a bad combination. He ran left towards a cliff face. He had magic Could he kill it? He threw a projectile at the creature, it certainly seemed dazed by the impact. Jack took the opportunity to fire a few more bolts at it. The creature eventually fell over. It was probably dead. Jack sighed. All that magic took the wind out of him. He walked back to the house. When walking back he felt a grip around his leg.

The creature was feinting death. It grabbed Jack and threw his towards a nearby tree. He hit it hard. He could taste blood. This wasn't the magical duel he had with Celestia. This was the real deal. He decided to try the move that Celestia pulled in a last ditch effort. He put both his hands together and summoned a large ball. After about the size of his head. He threw the ball directly at the bear's head. It hit, and the bear was sent flying onto it's back. Jack was dizzy. He felt the same feeling he did when he teleported twice. Sure enough, In a few seconds. He was unconscious.

Jack awoke in his house. His friends were waiting around him. He rubbed his head.

"Damn... What happened?" Jack asked.

"You almost killed yourself with magic again. Granted I suppose. You were kind of fighting an URSA MAJOR." Twilight said.

"Ursa what-now?" Jack asked.

"An Ursa major, one of the most dangerous creatures in Equestria. You killed it but almost killed yourself in the process." Twilight explained.

"Ah'll be honest Jack, I've never seen anyone stand up tall to an Ursa major before!" Applejack said.

"Oh yes, that was very dangerous." Fluttershy stated.

"Look at the state of your hair!" Rarity shouted. Jack was still dizzy.

"I suppose it's more sleep for me then." Jack stated.

"Yes, you should probably get some sleep right away." Twilight said. All of them albeit Rainbow left.

"How did they find me?" Jack asked.

"You were gone for a while so I went outside and saw you on the ground next to an Ursa." Rainbow said.

"You saved me..." Jack said.

"Yeah, I did." Rainbow said.

"...Thanks." Jack said.

"No problem!" She said.

"I'm gonna head to bed now." Jack said.

"I probably will too." She said back. Jack sighed and took out his dossier.

_Entry 15_

_So I'm dangerous now according to the townsfolk. I was gonna lay low for a while and I went exploring in the forest, In came across this big thing called an "Ursa major." Anyway, I almost killed myself with the amount of magic I used. So yeah, I'm pretty damn tired._

_-Jack Tailor_

**Yay! Weekend. My favorite time of the week. Anyway, Some announcements. I will be uploading the chapter on Monday _Very late at night_ because I'm going to meet my sister and my brother and catch up with stuff. So yeah. Credit to Redoktober for giving me the inspiration to write this fanfic. And... Yeah. No more else to add. Peace.**

**-Cupzy**


	16. Decisions, Decisions

Jack awoke. He had a headache from his "encounter" yesterday. Rainbow was once again cuddled up next to him. She had taken yesterday's talk into consideration. He smiled, he gave her a tap on the head.

"Dash, wake up." Jack said. He heard a disgruntled moan come from her. She eventually yawned and sat up on the bed.

"You call me lazy..." Jack said. Rainbow let out a small giggle.

"You feeling any better from yesterday?" Rainbow asked.

"I've got a headache but I'm alright." Jack said.

"Maybe you should stay in bed, maybe I can go downstairs and make you something?" Said Rainbow.

"As much as I would love to see you trying to operate a toaster, I think my house can go one more day without burning down." Jack said. He stood up, still slightly dizzy. They both walked downstairs. Jack proceeded to make four slices of toast for him and Rainbow. He set the two plates down on the table.

"So, what are you gonna do today?" Rainbow asked.

"I'll probably go see if Ponyville is still scared of me." Jack replied.

"Wouldn't it be better if you stayed in bed? I mean you kind of killed an Ursa major..." Rainbow said.

"Nah, if I stayed in bed all day you would have probably had nothing to do but sit next to me all day, am I right?" Jack asked. Rainbow blushed a little.

"Yeah, I guess..." She said. Jack stood up.

"Well, I'm heading into Ponyville, wanna come along?" Jack asked.

"Yeah, I've got nothing else to do today." Rainbow said. She held onto his trouser leg and Jack snapped his fingers. They were now in Ponyville. The residents seemed to ignore Jack so at least that was a plus. Suddenly something fell onto his head. A letter fell to the ground. He looked up, a grey Pegasus was waiting above them, she landed on the ground.

"What the hell? Who are you?" Jack asked, picking up the letter.

"My name's Derpy Hooves, nice to meet you." Derpy said. That's when Jack noticed that she was cross eyed.

_"Derpy Hooves... Really?" _Jack thought to himself.

"I'm the mail carrier around these parts." Derpy continued.

"I see, couldn't you have given me the letter, instead of dropping it on my head?" Jack asked. Derpy was silent for a moment

"It didn't land on your head. I gave it to you just now." Derpy said. Jack looked at the pony oddly.

"You must not have a good memory mister." Derpy continued. Jack frowned.

"Anyway... Thanks for the letter Derpy." Jack said. She went silent again.

"My name's not Derpy. My name's Ditzy doo, nice to meet you." Der-Ditzy said with a smile.

"B-but you said... that you- ah, never mind." Jack said as Ditzy flew away. He opened the letter.

_Dear Jack_

_I hope this letter finds you in good health. I would very much enjoy if you could drop by my house sometime today and we could have a chat. Also, Nightmare Night is coming up soon. I do hope you know what that is. Rainbow Dash will likely fill you in._

_-Twilight Sparkle. _

"Nightmare moon? What's that?" Jack asked.

"It's where we go around in costumes and get candy from other ponies." Rainbow explained.

"Halloween, essentially." Jack responded.

"Hallo- what now?" Rainbow said with a perplexed expression on her face.

"Never mind, aren't we a bit old for that?" Jack asked.

"You're never too old for nightmare moon! I don't really get candy though, I just go around and pull pranks on people." Rainbow said with a smile.

_"Classic Rainbow Dash." _Jack thought to himself.

"Oh yeah! Last year Luna broke free from her prison! She was called Nightmare moon back then. She tried to enslave us all but I just used my awesome skills to turn her back to the alicorn you see today." Rainbow said, striking a pose.

"I'll believe that when I see it." Jack said. Anyway, let's go drop by Twilight's place." Jack said. Rainbow nodded and to walk towards the town library. Once they had eventually reached the library. Jack knocked on the door. Twilight answered and smiled as soon as she saw Jack.

"Ah, hello Jack! Oh, I see you've brought some company." Twilight said as she looked at Rainbow Dash.

"She goes wherever I go." Jack said. Rainbow punched him on the shoulder with a grin.

"Well come in! Make yourself at home." Twilight implored. It had been a while since Jack had gotten a good look at the library. For once, books weren't scattered across the floor due to Twilight's recent studies.

"So are you two excited for nightmare moon?" Twilight asked. They both nodded.

"I don't exactly know the customs but it's nice to know that Equestria shares holidays with earth I suppose." Jack said.

"Oh, do humans have a nightmare night too?" Twilight asked, eager to learn more of Jack's culture.

"Sorta, but we call it Halloween." Jack said. They all sat around each other in a circle.

"So Rainbow Dash, how is it living with Jack?" Twilight asked. Afraid that she'd just barged into something personal.

"The actual _living _part of it is awful. The bed isn't as comfortable as the ones in Cloudsdale, and he eats some really weird stuff that you put in a bowl, then you cover it with milk."

"I'm heartbroken, that bed was expensive..." Jack said with a chuckle.

"But you two are happy with each other. Right?" Twilight asked.

"Very. Although she can be a brat at times she has a good heart." Jack said, he was rewarded with another punch from Rainbow.

"And vice-versa..." Rainbow said. She could feel a blush coming on.

"That's nice, if you don't mind me asking. Do you two intend to take your relationship... Further?" Twilight asked. Rainbow was taken aback, they both didn't know what kind of advancement Twilight actually meant... Jack just sat with his head down in embarrassment. Twilight was also a deep red after examining their expressions.

"N-no! Not like that! I meant, like... Marriage." Twilight said. Both of them looked at each other, as if trying to see into the others mind.

_"I... I like him, but would he be okay with something like that?" _Rainbow thought to herself.

_"Awkward, I mean, I LOVE her but... I'm not sure if she would be okay with something that big... She is Rainbow Dash, after all." _Jack also thought. Twilight felt guilty for both of them.

"I-I'm sorry, I crossed the line." Twilight said.

"It's nothing, it's given me something to think about..." Jack said.

"Wait, what?! I don't have time for marriage or any kind of soppy stuff like that! I'm Rainbow Dash! I have more important things to worry about!" Rainbow said, desperately trying to defend her reputation. Deep down she knew that she wanted to be together with Jack. 77

"Do you want me to give you two some space?" Twilight asked.

"It's fine Twilight. I think me and Dash will have a talk about it sometime in private." Jack said. He was afflicted by Twilight's words. He liked Rainbow Dash, he wanted them to be together. But he couldn't read her mind, he would have a talk about it tonight.

"We should head back..." Said Rainbow.

"Yeah, we should." Jack replied.

"It's been nice talking with you." Twilight said as Jack teleported him and Rainbow back to their house.

"So I guess you wanna talk about stuff..." Rainbow said.

"I don't know, you seemed pretty reluctant back there." Jack said.

"You know I didn't mean that!" She replied.

"So, anyway. What do you think?" Jack said

"I don't know, I was trying to find out what you thought first." Rainbow said.

"I'm conflicted but I'm moving towards "yes" a lot." Jack said.

"Yeah... Me too." Rainbow replied.

"Anyway, this is no time to be thinking about that, it's pretty damn late." Jack said. Him and Rainbow went upstairs. Jack put on his PJ's and took out his dossier.

_Entry 16_

_16th entry huh? I've been here for a long time. I got a message from this retarded mail pony today, Twilight invited us over to her place and she told us that Halloween's coming up, lovely. So we went over and somehow we got on the topic of marriage between be and Rainbow. Marrying a horse, crazy right? But I'm actually gonna say yes on this one. She's nice, sweet, good looking (In Ponyville anyway.) and I really like her. _

_-Jack Tailor._

**Short chapter? Yes. Boring chapter? Yes. Sleepy Cupzy? FUCKING YES. Anyway, There we go. I made either A) A smart plot device or B) The worst decision since me making this fanfic on the first place. I hope at least one person likes this idea. But anyway, tomorrow's upload will be _Even later and probably shorter (ikr how could you get shorter than this) than this chapter. _Just giving a little heads up. Credit to Redoktober for giving me inspiration to write this piece of garbage. **

**-Cupzy**


	17. Confrontation

Jack awoke. For the last two days he was woke up by sudden movements to his side. It was Rainbow moving around in her sleep while cuddling up to him. Jack decided to leave her in bed. He went downstairs and proceeded to make himself some cereal. While he was eating it, he heard a knock at the door. He set his cereal down on the table. He opened the door expecting to see a pony, but instead he saw a letter on the grass. He picked the letter up and looked around, whoever delivered the letter left in a rush. Jack went back inside. He sat down on the couch and opened the letter.

_Dear Jack_

_If possible, sometime today I would like to talk to you in private. It concerns our talk yesterday. I would prefer if you came without Rainbow Dash._

_Twilight Sparkle._

_"Huh, what's there to talk about? The deed is done, I suppose." _Jack thought to himself. He decided to go. He had no idea why Twilight didn't want Rainbow to come along but he wasn't going to question her logic. He slowly walked back upstairs and slipped some decent clothes on without Rainbow noticing. He took a sticky note out of his wardrobe and took a pen out of his bedside cabinet. He wrote a note for Rainbow Dash explaining that he had gone to Ponyville to run an errand, reminding her not to use anything in the kitchen.

He stuck the note on the wall halfway down the stairwell. Anyone with a brain would be able to see that one their way down. Jack snapped his fingers and he appeared in Ponyville. The whole "Most powerful being in Equestria" thing had worn off on Ponyville. And they no longer considered Jack a threat, although some ponies still threw him glares. He made his way towards the library. He wondered if leaving Rainbow inside of the house was a good idea. He got to the library and knocked on the door. It was answered in moments by Twilight.

"Oh there you are Jack! Come in!" She said. Jack walked inside of the library. He pulled up a chair.

"So, what did you want to talk about?" Jack asked.

"Well, I said that I was going to talk to you about the whole... Marriage... thing." Twilight replied. Jack shifted in his chair a little.

"What about it?" Jack asked.

"Well, I understand that you two like each other but you haven't even known each other for three weeks yet! It just seems a little... Rushed." Twilight said.

"Look, Twilight. We both haven't decided on it yet. It might not happen at all. There's no need to get so worked up about it." Jack said.

"Alright, while we're on the subject, can we talk about... Us... for a second?" Twilight asked. Jack was taken aback. He now knew why she didn't want Rainbow coming along.

"Well, what's left to say on the subject?" Jack said, head hanging low.

"Well, it didn't last for very long did it? Did you... Just... Not like me anymore?" Twilight asked. Jack didn't know how to answer. He dumped her simply because of the situation with Rainbow Dash. But if he told her that, he would be essentially saying he doesn't like her.

"I just... Wasn't really ready yet, you know?" Jack said.

"But you started going out with Rainbow Dash a couple of days later!" Twilight replied.

_"More like a couple of hours later..." _Jack thought to himself.

"I just..." Jack cut off, he didn't have any sort of excuse. There was no other way to say it, he just liked Rainbow more.

"You just what?" Twilight replied. There was no other way out. He could tell her the truth or just teleport away, but that wouldn't leave a very good lasting impression...

"Okay, I'll tell you the truth." Jack said.

"Truth? What truth?" Twilight asked, intrigued.

"Okay, basically, Rainbow had her eye on me ever since I entered Equestria... I think. And she kept pestering me about it. After the Canterlot festival, while you and me were still... You know. We kinda... Uh... K-kissed." Jack admitted. Twilight was visibly shocked.

"So essentially, you were cheating on me?" Twilight asked with a hint of menace in her voice.

"Cheating's taking it a little far. It was one kiss. She talked me into it." Jack explained. Twilight was as white as a ghost.

"So... You dumped me... To be with her?" Twilight asked. Jack gulped, there was certainly no easy answer to this question.

"...Y-yeah..." Jack said. The room was silent for a few moments. Twilight had a look of despair in her eye. She felt like she had been played for a fool. Eventually Jack spoke up.

"Uh... You okay?" Jack asked.

"..." Twilight said nothing. Jack took her silence as permission to leave.

"I'll... Leave..." Jack said. Twilight gave a small nod and Jack snapped his fingers, reappearing outside of the library, he couldn't bear just walking out. He had just left Twilight with her heart broken for the umpteenth time. He lowered his head and started walking back towards his house. He couldn't teleport, he used the last of his magic preserving his sanity. He walked back through the forest until he finally came back home. He opened the door to see Rainbow on the couch, dozing. She woke up when she heard the door opening.

"Huh? Who's there..." Rainbow said, still tired.

"It's me." Jack said.

"Oh, It's just you. You look depressed." Rainbow replied. Jack sat down on the couch next to Rainbow.

"I uh..." Rainbow was at a loss for words at Jack's silence.

"I... Had to tell Twilight about what happened between me and her..." Jack eventually said. Rainbow pulled a dumbfounded expression before finally changing to a surprised look.

"You did WHAT?!" Rainbow shouted.

"Yeah, she didn't leave me with an easy choice." Jack said.

"Oh my gosh... Don't you understand what you've done?! You've broke Twilight's heart! AGAIN!" Rainbow wailed.

"Like I said, it wasn't an easy choice to make..." Jack replied. Rainbow was shivering.

"Oh man... This messes up everything. It was going so well..." Rainbow said.

"This was worse than when Celestia broke her heart. That time she sunk into depression... For a short while..." Jack said. They both sat in silence. Pondering over what move they should make.

"Yeah, but don't you understand?" Rainbow said.

"Hm?" Jack replied.

"I represent the element of loyalty. LOYALTY! And I broke one of my best friend's hearts..." Rainbow said. Jack remembered what Twilight had told him. The elements of harmony, Twilight and every one of her friends represent one of the elements of friendship...

"What's the worse that could happen?" Jack asked.

"WHAT'S THE WORSE THAT COULD HAPPEN?! How about I'm not one of Twilight's friends anymore?" Rainbow said with a tear in her eye.

"Look, she'll pull through, you've had troubles with each other in the past right? You fell out at certain point... remember what happened with that... Uh... Discord guy?." Jack asked.

"That's because he essentially brainwashed us!" Rainbow shouted.

"But if I recall what Twilight told me, she said that you were the most stubborn of the bunch. But they still forgave you in the end..." Jack said.

"Yeah... I suppose..." Rainbow said. Sniffling.

"Even if we can't get the uh... Marriage thing sorted out..." She continued.

"That can wait." Replied Jack. Jack looked at the time. Even though only a short amount had happened today, the time was already 7 o clock. He started to make some dinner for the two. Jack just lived off breakfast and the occasional salad for food sources. Maybe he could actually make some dinner for once. He didn't know a lot about cooking but he knew enough as to not burn him or the house down in the process. He made some bacon for himself. He didn't know exactly what Rainbow liked to eat so he just made her some pasta.

He brought the two plates through and placed them on the table. Rainbow gave Jack an odd look. As if he was making a joke.

"What's that on your plate..." Rainbow said with a horrified expression. Jack cursed. The ponies were herbivores so seeing something eating meat was essentially like watching a cannibal.

"Oh crap, I'm sorry. It's uh... Meat." Jack said.

"Meat?! How could you eat meat?!" Rainbow shouted at him.

"Humans are omnivores. We eat both plants and meat to maintain a healthy diet." Jack explained.

"That isn't... pony meat, is it?" Rainbow asked, getting slightly scared.

"No, do you have pigs in Equestria?" Jack asked.

"Oh... That's pig meat..." Rainbow said. Jack rolled his eyes. Him and Rainbow started eating their meals, she seemed to enjoy the pasta but kept shooting odd glances at Jack's plate. After both of them had finished Jack yawned.

"Well, I'm gonna head to bed." Jack went to the beginning of the stairwell but was stopped by Rainbow Dash.

"BED?! Jack, tonight's nightmare night!" Rainbow said. Jack's memory flashed back.

"Oh yeah..." Jack said, disappointed that he wasn't gonna get a good sleep tonight. He went back onto the couch and took out his dossier.

_Entry 17_

_So... I had to tell Twilight about the ah... Complications between me and Dashie. Anyway. She's probably really sad... Again. But tonight's nightmare night so I'm certainly not getting a good night's sleep tonight... Hopefully Twilight will be able to forgive me for today's events._

_-Jack Tailor._

**Another short chapter, yes I know. I didn't upload a chapter yesterday because I was tired after heading all the way over to Brighton and coming aaaaaalll the way back... Oh yeah! Some stuff's gonna happen. Chances are I won't be able to submit a chapter from Wednesday to Friday 'cause I'm going over to my best friends house. And uh... He knows I'm a brony but doesn't know I write THIS. And if he found out I would never hear the end of it. Credit to Redoktober for inspiring me to write this fanfic. Peace :3**

**-Cupzy**


	18. Nightmare night

Jack stood up. He slipped his dossier into a cabinet. Rainbow was showing her excitement for nightmare night.

"I can't wait! Imagine all the pranks I could pull on ponies! And how much candy I'll get! I left my costume back at my house though so I guess I'll just rely on you for that!" Rainbow said excitedly. Jack still hadn't met the large majority of Ponyville, although most had seen him during the incident with the fallen Pegasus.

"More importantly, how long do you intend to do this for?" Jack asked. Rainbow thought for a moment.

"All night?" Rainbow replied.

"Aren't most ponies going to bed at that time? We'll go out until around twelve-ish and then head back, okay?" Jack said.

"Yeah, that sounds like a good plan." She replied. Rainbow was jumping around Jack's house like it was Christmas morning. He was still worried about Twilight. He was surprised that Rainbow managed to shake it off so easily. Hopefully he wouldn't run into her. The duo emerged from the house. The shrieks of small fillies could be heard all the way from Ponyville. They started progressing through the forest, while Rainbow was focused on things like candy. Jack was worried about what would happen if he ran into Twilight. Has she told her friends? Will she hold a grudge for long?

In Ponyville, some ponies had decorated their houses with ordinary Halloween decorations. Young ponies were rushing from house to house in an assortment of costumes. Some of the older mares and colts wore costumes depicting famous ponies rather than generic costumes. Rainbow was eagerly looking around, she spotted a group of fillies, a smile formed on her face.

"I'll be right back, alright?" Rainbow said.

"Sure, don't do anything stupid that'll attract a bunch of attention, I still don't know how Twilight's gonna react to all of this..." Jack said. Rainbow gave a nod and flew in the direction of the fillies. Jack walked in the opposite direction, shortly afterwards hearing the sound of rain and a mixture of laughter and screams. Almost everypony that was outside had a costume on. Jack assumed being an entirely different species counted as a costume. He managed to spot a few of his friends in the midst of the crowds. Still no Twilight. Maybe she didn't come out at all.

Meanwhile, Twilight was lying on her bed with her head on the pillow, crying her eyes out.

"How could Jack do this to me?" She said among some tears and sniffles. She could hear the commotion from Ponyville from her window. Her friends were probably wondering where she was. She heard someone open the door.

"Um... Twilight? Are you okay?" A familiar voice said.

"I'm fine Spike. Just leave me alone..." She replied.

"But it's nightmare night! It's essentially a crime to not enjoy tonight!" Spike said.

"If you want to go find the girls then you can, I'm not going to hold you back." Twilight said. Spike was already gone, he heard the front door slam. She sighed.

_"Of all nights, of all the days he could have chosen to break my heart, he chooses nightmare night... The girls are probably worried about me, Spike will probably tell them the reason..." _Twilight thought to herself. How could Jack just dump her then immediately start dating another pony? And one of her friends, at that. There was no need for depression on nightmare night. She got out of the bed.

_"I'll go outside, maybe the festivities will cheer me up... I just hope that Rainbow didn't drag Jack along for nightmare moon. Seeing him would just provoke me..." _Twilight thought to herself. She walked downstairs and opened the front door, it didn't matter if she didn't have a costume. She closed the door behind her.

Meanwhile, Rainbow had gotten Jack to accompany her to the large majority of houses in Ponyville to see how much candy she could get, nightmare moon certainly seemed to be one of Rainbow's favorite holidays. When they had finally got enough candy to fill up Jack's rucksack, they finally started to head home.

"I don't care if I have to hold you down, I'm not going to let you eat all of this at once. The last thing I want to see is Rainbow Dash on a sugar rush." Jack said. Rainbow let out a giggle. Jack started thinking about Twilight again, it seemed like she didn't come outside. Jack was too lost in his own head that he walked straight into a pony, knocking Jack off balance.

"I'm sorry, I wasn't looking where I was going." Jack apologized as he lifted himself up. He looked at Rainbow, she had a horrified expression on her face. Jack looked forward, he had knocked over Twilight. She was still picking herself up, not knowing who knocked her over.

"It's not your fault, I was also deep in thought." Twilight said. She looked up and stepped back. All that could be heard was the commotion coming from the town. Jack had his head hung low, Twilight had went back to a menacing glare. Rainbow stood in between the two.

"Look. I-I'm sorry, okay? Why can't we just put this all behind us? For tonight at least." Jack said. Twilight remained silent. She started walking past Jack, back to her own house.

"Hey! Giving me the silent treatment won't fix anything! Why don't you just talk about this?" Jack asked. Twilight turned her head around to look at Jack.

"What's there to talk about? What's done is done. It would be for the better if we didn't talk much Jack." Twilight explained.

"That's not true..." Jack said. Twilight began to walk away again. Rainbow tugged at Jack's leg.

"Come on Jack, let's go home." She said.

"You go. I'll be right there." Jack replied. Jack started walking towards Twilight's library. He needed to stop this, all he wanted was to be happy with Rainbow Dash and Twilight was making it difficult. When he finally reached the library he knocked on the door. Spike answered.

"Sorry Jack, Twilight told me not to let you or Rainbow Dash inside." Spike said.

"Spike. This is serious." Jack said. Spike gulped and let Jack inside. He walked upstairs. He put his ear up to the door and heard the faint sounds of crying. He knocked on the door.

"Twilight, we need to talk." Jack said.

"Go away..." Is was Jack could hear through faint mumbling.

"Staying in your bedroom isn't going to help anyone. We need to talk about this." Jack replied. He heard the sound of hooves clopping on the floor, shortly after he saw a small crack open in the door.

"What do you want?" Twilight said.

"I think you know what I came here for." Jack said. He heard the sound of a chain and then the door opening. Jack walked inside.

"I told you before, there's nothing left to talk about." Twilight said.

"I just want you to accept me and Rainbow's relationship. I know it may be hard considering I... Cheated on you..." Jack said.

"It's not that you started going out with Rainbow it's just that... You made be feel betrayed..." Twilight replied.

"Twilight. I just want you to be happy again. The reason I'm talking to you right now is because I don't want you to feel betrayed anymore." Jack said.

"But... I thought you hated me..." Twilight said.

"I never hated you Twilight, it was just Rainbow's persistence that won me over." Jack explained. Twilight remained silent, thinking about Jack's last sentence.

"Okay... I forgive you." Twilight eventually said. This caused a smile to form on Jack's face.

"Thanks Twilight." Jack said. He started walking to the front door.

"Oh, and Jack?" Twilight asked from the stairwell. Jack looked back, she was smiling for the first time in a while.

"Yeah?" He replied.

"Are you still going ahead with the whole... Wedding... Thing?" Twilight asked. Jack was dumbfounded, he wanted to at least get to know Rainbow a little more first. But it did seem like Rainbow was enthusiastic about the idea. Jack remained silent for a few moments.

"I'll... Think about it." Jack eventually said. Twilight nodded and waved to Jack as he left.

At Jack's house. Rainbow was trying to eat as much candy as she could before Jack came home. After a few moments however, she heard the door opening.

"I told you not to eat all the candy..." Jack said. Rainbow shrugged and continued eating. Jack took his dossier back out from the cabinet. He walked upstairs and put on his PJ's.

_Entry 18_

_Two entries in one day... Crazy right? Anyway, I had another talk with Twilight. After explaining a few details to her. She finally managed to forgive me for everything. She mentioned stuff about a wedding between me and Rainbow, I'm still thinking about it. Rainbow's gonna be on a sugar rush for the next couple of hours so I'll talk about it to her tomorrow._

_-Jack Tailor._

**OMG. I'M NOT DEAD. YAY! Anyway, yeah... I was at my best friends house for a couple of days so I couldn't actually write anything. I know this chapter is pretty damn short. But I'm back so I can write fanfics everyday again. yay. Credit to Redoktober for inspiring me to write this fanfic. Peace.**

**-Cupzy**


	19. (Insert chapter name here)

Jack opened his eyes, Rainbow was in her normal position. She probably went to sleep a few hours ago. Jack got up and put on a black T-shirt with jeans. He went downstairs and proceeded to make himself some toast. He started thinking about what Twilight said yesterday. Was a wedding in order? No. It was way too early on in their relationship. Jack just needed to see Rainbow's reaction, he wanted what was best for her. After eating the toast. He heard the familiar tapping of hooves on the staircase. She was walking down the stairs very slowly. She was having trouble keeping her eyes open.

"Good morning Dashie." Jack said with a smile. Rainbow just grumbled and sat down on the couch.

"If you say "I told you so" I'm gonna move out..." Rainbow said with her eyes half open.

"How much of it did you eat?" Jack asked.

"Um... All of it." Rainbow replied. Jack's jaw dropped.

"We literally visited almost EVERY SINGLE house in Ponyville, took nearly every ounce of sugar in their households and you're telling me you ate ALL of it?" Jack said. Rainbow nodded.

"I am never going outside with you on nightmare night again." Jack said. Rainbow let out a small giggle and made herself comfortable on the couch.

"I had a talk with Twilight..." Jack said. Rainbow sat bolt upright on the couch.

"And what did she say?" Rainbow asked.

"She said that she forgives us." Jack said. Rainbow let out a large sigh.

"That's a relief." Rainbow said.

"Yeah. But now, something else is on my mind..." Jack said.

"What's that?" Rainbow replied.

"It's about that whole... Marriage thing." Jack said. Rainbow blushed a little.

"You can't actually be thinking about that, right? I mean, I can't be tied down with someone like YOU." Rainbow said. Jack sighed.

"You... Already kind of are." Jack explained. Rainbow stuck her tongue out at Jack. Rainbow was thinking about it as well. Even though they had only be seeing each other for only a couple of weeks, marriage wasn't actually a bad thing to consider. Although she did want to keep her tomboy reputation up, she also really wanted to be together with Jack.

"Well... I mean, I like you. But..." Rainbow stuttered.

"But what?" Jack replied. Rainbow was at a loss for words for once. She couldn't think of any kind of contradiction to the marriage idea.

"Uh... Never mind. I was just rambling to myself again." Rainbow said with a nervous laugh. Jack gave her an odd look and shrugged his shoulders.

"I'm just glad that Twilight forgives us. Maybe I could have a normal day for once. I'm gonna head into Ponyville to get some food. I'm gonna run out in a few days time." Jack said.

"Alright, I'll just... Keep an eye on the house while you're gone." Rainbow said, yawning. Jack snapped his fingers and appeared outside of sweet apple acres. He needed to buy some apples. He walked inside the farm and noticed Applejack coming out of the barn.

"Hey Applejack!" Jack shouted. She looked in his direction and gave him a wave. Jack started walking over to her.

"Hey there Jack! What can ah do for ya?" Applejack said.

"I'm running out of food in my house, I was hoping you could sell me some apples." Jack explained.

"Well, sure thing sugarcube! How many do ya need?" Applejack said. Jack started counting on his fingers.

"I think about 2 dozen should last me for a while." Jack said.

"Sure thing, ah'll let ya have the first batch for free. The second batch is gonna cost ya thirty bits." Applejack said. Jack had been getting a share of Rainbow's wages. Because his house didn't actually cost money they had a lot of it spare. He took his wallet out from his pocket and took out the necessary bits. He handed them to Applejack.

"Thanks sugercube, ah'll go and get them apples for ya." Applejack said. She walked off and returned a few minutes later with a sack of two dozen apples.

"Thanks for the help Applejack." Jack said.

"It's no problem Jack." She replied. Jack gave a wave as he walked back to Ponyville. He had nothing else to do. All of his worries had been resolved. He decided to pay Twilight a visit and see if she needed help with anything. He walked to the library and knocked on the door. Twilight answered with a smile.

"Hello Jack, what brings you here?" Twilight asked.

"I have nothing else to do, do you need any help with anything?" Jack answered.

"You could help me re-organize all of my books. I think Spike's a little tired out." Twilight said. Jack looked inside to see a very exhausted Spike.

"S-she's done it five times already... Please Jack, take over for me..." Spike said as his head collided with the floor. Twilight let out a small giggle.

"Alright, I'll help you." Jack said. He could hear a faint "Yay" from Spike. Jack and Twilight spent the next hour making sure all of the books were well organized.

"Hey Jack?" Twilight said.

"Yeah?" He replied as he picked up a book.

"What did Rainbow say about the marriage thing?" Twilight asked. The question took Jack by surprise, he dropped the book and looked embarrassed when he picked it back up.

"I, uh... Well... She seemed pretty... I don't know. She looked like she wanted it to happen, but kinda didn't as well." Jack said.

"That sounds like Rainbow Dash to me, always trying to protect her reputation." Twilight said. Jack chuckled.

"I think she's just touchy about the subject. I mean she said that she liked me but... And she just kind of trailed off at that point." Jack explained.

"I'm sure she's just embarrassed, she's never really had a coltfriend before." Twilight said.

"Coltfriend? I'm not a pony Twilight." Jack said. Twilight laughed for a moment.

"Either way, she's been happier ever since you entered Equestria." Twilight said.

"Considering the fact that she met me via breaking one of my windows..." Jack said with a chuckle. It took them another hour to make sure all of the books were in the correct places. Jack was pretty tired at the end.

"You... Did that five times over?" Jack asked.

"Yeah. I guess you could call me a perfectionist." Twilight said.

"I think it's called obsessive compulsive disorder. I'm probably gonna head back to my house now." Jack said.

"Alright, I'll see you tomorrow." Twilight said as Jack left the library. He started walking back to his house. Maybe Rainbow had done some cleaning up in the meantime. Jack shook his head. No. That was impossible. He walked through the forest until he finally came to his house. He looked inside the window. No sign of Rainbow. He opened the door.

"Hey! Dashie! I'm home!" Jack shouted. No reply. He walked inside and upstairs. Rainbow was on the bed. Fast asleep. He went up to her and poked her on the head.

"Hey, dash. Wake up, you'll wake up in the middle of the night if you keep sleeping." Jack said. He heard a slight "Urgh" from Rainbow and he realized she must be feeling the aftermath of all that candy. She had her hooves over her stomach and had a painful expression on her face. Jack facepalmed.

"I told you not to eat all the candy..." Jack said. Rainbow waved one of her hooves in Jack's direction. He put on his PJ's and went into bed.

"So, I talked to Twilight again about the marriage thing." Jack said.

"You did?" Rainbow said in between grunts of pain.

"Yeah, we both agree that you're just embarrassed about the situation." Jack said. Rainbow sat upright in the bed.

"Me?! Embarrassed? Yeah right! I've got much more important things to worry about than marriage!" Rainbow exclaimed.

"Like what?" Jack asked with a smile.

"Well, uh... I gotta... Train for the uh, wonderbolts... and I've gotta... Uh..." Rainbow trailed off before sinking bad into the bed in pain.

"I suppose we could ask some of Twilight's friends about it..." Jack said. This provoked another reaction from Rainbow Dash.

"Woah. Woahwoahwoahwoahwoah. We can't just go around and tell people about us. Some of Twilight's friends don't even know we're dating!" Rainbow said.

"Yeah, that's true." Jack pondered.

"Well anyway, I'm too tired and in pain to talk about this so just go to sleep... Please." Rainbow said as she sunk into the pillow. Jack chuckled and took out his dossier.

_Entry 19_

_So, everything's going alright actually. Twilight asked me about the whole "marriage" thing and I told her that we still haven't decided yet. I'm still worried about, well, you know, marrying a PONY. and Rainbow wants to defend her reputation. Rainbow's still sick from nightmare night so maybe that wasn't the best time to talk about it._

_-Jack Tailor_

**So... Yeah, nothing really important to say right now... I know I'm going a bit all-out with this marriage thing but the truth is I want to start writing a new fanfic ASAP because I've got a slightly less crappy idea for a pony story. So yeah... Credit to Redoktober for inspiring me to write this fanfic. Peace.**

**-Cupzy**


	20. Shush It's a surprise

Jack opened his eyes. Rainbow was cuddled up next to him per usual, he moved out of the way which also caused Rainbow's eyes to open. He heard a yawn.

"Isn't it a bit early to get up?" Rainbow said to Jack. He looked at the clock. It was 9 o clock.

"It's not that early. I was going to head into Ponyville to get some more food. We can't live off apples alone." Jack said.

"Man, you sure do overwork yourself." Rainbow said.

"Well, technically you're the one who's making us the money." Jack said.

"Yeah, we have tons left over because we don't actually have to pay bills or anything." Rainbow said. Jack walked downstairs and started to make toast for him and Rainbow. He heard a knock coming from the front door. He answered to see Ditzy doo standing there.

"Hey Ditzy Do. What are you doing here?" Jack asked. Ditzy pulled an odd expression.

"Ditzy Do? Who's that? Have you forgotten my name? It's Derpy Hooves. Nice to meet you!" Derpy said. Jack rolled his eyes.

"Anyway... What are you doing here?" Jack asked.

"Have you forgotten? I'm a mail carrier! You might wanna get that memory checked out mister..." Derpy said with her head tilted. She pulled a letter out of her bag and handed it to Jack.

"Thanks Derpy." Jack said.

"...It's Ditzy. But it's alright, people forget things like that. Bye!" Ditzy said as she flew away. Jack broke the seal on the letter and began to read it.

_Dear Jack_

_I have been recently informed of your current relationship status with the mare Rainbow Dash from Twilight. I hope for the best that you two decide what is best for each other. However, you must know that a marriage this early on in your relationship may provoke some unusual reactions from the citizens of Equestria, I simply wanted to warn you about this. I hope that the situation turns into something you can cherish for the rest of your life._

_-Princess Celestia _

Jack was surprised at the letter, not only did he not expect that Twilight would tell the princess, but she wrote the letter as if the two of them were already engaged.

"Hey! Dashie! You'd better take a look at this." Jack shouted upstairs.

"Coming..." Rainbow said, unenthusiastic to get out of bed. When she finally managed to reach the living room. Jack waved the letter in her face, prompting her to read it. After a few moments of Rainbow looking at the letter, her expression of tiredness had went to an expression of both intrigue and worry.

"I don't see anything really wrong with this letter." She finally said.

"The problem is that this marriage thing keeps getting brought up. It started off as a... Well, hopefully honest joke from Twilight but now it's actually got me wondering..." Jack said.

"Yeah, I did some thinking overnight and thought that we should really make a decision sometime soon." Rainbow said.

"I thought the female's opinion mattered more..." Jack said. Rainbow blushed a little.

"I mean... I-I'm alright with it it's just that..." Rainbow cut off once again.

"Because you're trying to defend your reputation?" Jack said.

"Y-yeah! I worked hard to get where I am." Rainbow said.

_"_By "worked hard" you mean that you're training to get into a group of professional flyers?" Jack said.

"Hey! The wonderbolts just haven't recognized my potential yet! Once they see how I fly they'll be on their knees begging me to join them." Rainbow gloated. Jack rolled his eyes.

"Your reputation won't be dragged down simply by marrying someone, realistically, you should gain respect from marrying someone." Jack explained. Rainbow took a few seconds to process the information she had just been fed.

"Is... That true?" Rainbow asked.

"Of course it's true." Jack responded. Rainbow looked like she was having a battle with her subconscious in her head. Jack went to go fetch the toast while Rainbow sat on the couch. He came back with burnt toast. Rainbow was still looking at him with an odd expression.

"Hey Jack?" Rainbow eventually asked.

"Yeah?" He replied while biting into the toast.

"Do you like me as much as I like you?" Rainbow asked.

"I think the correct word you're looking for is love, not like." Jack responded.

"Yeah, yeah. Anyway, your answer?" Rainbow asked.

"Well yeah, of course I do. If I didn't then you wouldn't be in my house right now. Of course I love you." Jack said. This made Rainbow smile. She moved across the couch and hugged him. In a few moments, Jack found himself locked in another kiss with Rainbow. This one felt more... Intimate than the others, she pulled out after a few minutes with a large smile on her face.

"I love you." She said while giving Jack another hug. He smiled.

"I love you too." Jack replied. Jack had gotten past the whole "pony" thing and just learned to live with it. He was really happy with her in his life. He preferred his life in Equestria more so than on earth. He had never had a girlfriend. Hell, he never really had any friends in general. But all of his problems were fixed when he came into Equestria. The two just stared into each others eyes for a while.

"I suppose this means you're alright with the whole wedding thing." Jack said with a smile. Rainbow nodded in response.

"Well, if it's what's best for you then I'll do it." Jack said. This was he happiest he had ever seen Rainbow get, she had gotten over her reputation and decided that she just wanted to be together with Jack.

"We might as well go tell everyone..." Rainbow said with a blush.

"Yeah, let's go tell Twilight, she'll pass the word on." Jack replied. He stood up and stretched his arms, Rainbow held on to his trouser leg as he snapped his fingers. They were transported to the outside of Twilight's library. The time was still early afternoon but Twilight would probably be awake by this time. He knocked on the door. Twilight answered moments later.

"Hi you two! What brings you here so early in the morning?" Twilight asked.

"Uh... We have something to tell you. Don't worry, it's good news." Jack said. Twilight invited them inside. All three of them pulled up chairs to a circular table near the corner of the library. Jack spent the next good hour telling Twilight about their decision. By the end of it, Twilight had a smile on her face.

"Wow! I'm really happy for you two! Do you want me to tell the rest of the girls?" Twilight asked.

"If you could." Jack responded. Twilight made a large mental note to tell all of her friends about the situation.

"Well, I'm very happy for you two! I uh... G-guess this has something to do with the letter that I sent to the princess this morning?" Twilight asked.

"Yeah, it really got us thinking about it, so I suppose we have you to thank Twilight." Rainbow said.

"Just remember, when this gets into the hands of Pinkie and Rarity then it'll probably be all over Ponyville in less than a day..." Twilight said.

"Uh... Tell them last then." Jack said. They got up from their seats and waved goodbye to Twilight. Rainbow was ecstatic about the event. But started to question her decision later on.

"Oh my gosh! What will the wonderbolts think about this?!" She said to Jack.

"I'm pretty sure this will probably never reach their ears until the actual wedding day. Plus why would they have a negative view on you getting married?" Jack asked.

"Because they'll think that I'm gonna get dragged down by being with you all the time!" Rainbow said. Jack chuckled a little.

"I doubt it." Jack replied. This made Rainbow calm down a little. While they were walking just about to leave Ponyville, they heard the faint clopping on hooves behind them. Jack turned around to reveal Pinkie Pie. Who instantly lunged for Jack's face. He dodged out of the way just in time.

"Oh my gosh I can't believe that you two are getting married!" Pinkie shouted.

"Yeah, we are. an odd couple." Jack said, Rainbow punched him in the leg.

"Do you two understand how big of a party I've got to throw now? This is gonna be one for the books!" Pinkie Pie shouted. She excitedly hopped away rambling about balloons and cupcakes.

"Maybe it would've been better if Twilight didn't tell her..." Jack said.

"Hey, this is a good thing! You haven't lived if you haven't been to one of Pinkie's parties." Rainbow said. Jack had never actually been to any of the countless parties that Pinkie had thrown. He shuddered to think of Pinkie's idea of a wedding party. They continued to walk through the forest until they came back to Jack's house. He walked back inside and sat back down on the couch. The next few days were going to be hellish. And he needed to enjoy every second of relaxation he could get form her on out. Just as he sat down, however, there was a knock on the door.

"I'm never going to get any time to myself today." Jack pouted as he opened the door. Rarity was standing there.

"Oh, hello Rarity! What brings you here?" Jack asked. Stupid question.

"Pinkie Pie came rushing up to me looking positively overexcited and told me that you two were engaged to be wed. Is this true?" Rarity asked, a hint of disbelief on her face.

"Yes, it's true." Jack said. Rarity almost went to a Pinkie Pie level of excitement after she heard that. But she consoled herself after letting out a short giggle.

"That is lovely to hear Jack! I will finally have a project to work on during my free time. I will need to make a suit and a dress fit for a magnificent wedding!" Rarity exclaimed. This was the first time Jack had seen Rarity like this.

"You don't need to do it now, we don't even know what day the wedding's going to be on." Jack said. Rarity barely listened to a word he said, she was too busy mumbling to herself about ideas for the clothes.

"Oh, I'm sorry Jack, did you say something?" Rarity said.

"Never mind. Just... Don't overwork yourself, alright?" Jack said. Rarity nodded and started walking back to Ponyville, It was dark outside and Rarity nearly screamed when she stepped into a puddle. Jack chuckled and closed the door. The time was nearing eight o clock. The day flew in once he had left the house. He decided to get ready for bed. He walked upstairs where Rainbow was already half asleep on the bed. She must have been mentally exhausted with what had happened today, she had a smile on her face once Jack walked inside. He put on his PJ's and took out his dossier.

_Entry 20_

_Wow... It's been twenty days, huh? Well anyway, it turns out that I'm now engaged to Rainbow Dash, you may think I'm crazy but... If you were in this world, I think you'd understand the situation I'm in, Dashie couldn't be more happier, I've never seen her this happy in a long time. In a way, I'm happy too. This life is much better than my life in London, I only had my mother with me. And my social life, dare I speak of it, was terrible. But in Equestria, people are much happier, their lives are so much better, and unlike London, knife crimes don't occur every 5 minutes. _**(I made a London joke, please don't kill me.)**

_-Jack Tailor_

**So...Twenty chapter... Yay! Time flies when you're making shitty fanfics. So I've hit this story with quite a sudden plot twist that'll take a few days to wear off. Don't worry, I don't intend to end the story right away, probably during the next two weeks or so. Credit to Redoktober for inspiring me to write this fanfic. Oh and I forgot to mention something. I HAVE NEARLY 3,000 VIEWS OMG I AM ACTUALLY CRYING RIGHT NOW. PEOPLE ON THIS SITE ARE AMAZING. Also, two chapters in one day? Yeah, I was gonna give myself a head start for tomorrow but I figured "Ah, fuck it." and wrote a new chapter, I still intend to make one tomorrow. Peace.**

**-Cupzy**


	21. Preperations

Jack opened his eyes, feeling much happier than usual. He got up, he was probably going to spend most of the day organizing the wedding. He put on some clothes and went downstairs to make himself and Rainbow some toast. While he was waiting for his breakfast to finish, he heard a knock at the door. He yawned and answered it. Applejack and Fluttershy were standing at the door.

"Hi girls." Jack said. Applejack gave him a frown.

"We come all the way through the forest to congratulate you on your wedding and all ya'll got to say is hi girls?" Applejack said.

"Yes, we wanted to come and give our regards to you both." Fluttershy continued.

"I appreciate it. I'm probably not going to get much rest for the next few days." Jack said.

"Well, try not to overwork yerself sugarcube. We'll be supportin' ya all the way." Applejack said.

"Thanks Applejack. Dash isn't actually awake yet." Jack said.

"Ah'm not surprised, givin' that you two are gettin' married soon yer gonna need all the rest ya can get." Applejack said. The two of them turned around and started walking back to Ponyville, giving Jack a wave before they were out of sight. Jack was about to go back inside when he realized he was standing on a letter. He picked the now dirty letter up from the ground, it had the royal seal on it. Jack walked back inside and began to read the letter.

_Dear Jack_

_I have heard the news of you being recently engaged to Rainbow Dash, I am very happy with your decision. If you could send me a reply stating what day you desire the wedding to be on, it would be much appreciated. I imagine that Rarity and Pinkie Pie will also be helping you prepare for the wedding. I must warn you, Pinkie Pie's parties can be a bit... Over the top._

_-Princess Celestia._

Jack put the letter down on his table. He would have to go to Twilight's and ask her to write a letter to the princess. He heard Rainbow making her way down the stairs. She sighed.

"What's with all the noise?" Rainbow asked, still half asleep.

"Applejack and Fluttershy came to congratulate us on the wedding." Jack said with a smile.

"Wedding? What wedding?" Rainbow asked. Jack facepalmed. She had already forgot.

"Uh... We agreed yesterday that we would get married? How could you forget something that big?!" Jack said. Rainbow put her hoof to her chin and closed her eyes for a few moments, eventually she came to a conclusion.

"Oh yeah! I remember now! Sorry about that. I don't have a great memory." Rainbow eventually said.

_"Even Derpy could remember something like that..." _Jack thought to himself.

"Anyway... Has anything important happened yet?" Rainbow asked.

"I got a letter from Celestia asking what day we want the wedding to be on." Jack replied. Rainbow thought for a moment.

"Why can't we just have it today?" Rainbow asked.

"...Because that's rushing into things too fast." Jack replied. Rainbow nodded to show that she understood.

"Then... How about in three days?" Rainbow said.

"Yeah, that sounds reasonable. Hopefully Rarity will be able to make a suit and a dress by that time and... Hopefully Pinkie will be able to get all of the festivities ready. I've got to head into Ponyville to get Spike to send a letter to the princess." Jack said.

"Alright, just a heads up, it's supposed to rain today, so you might wanna get there quick." Rainbow said. Jack nodded and snapped his fingers, appearing in Ponyville. He began to walk towards Twilight's library. He had a few looks from the townsfolk, granted, considering that Rarity was told about the wedding it's no surprise that she gossiped to everyone. He eventually came to the entrance of the town library, he knocked on the door. Twilight opened the door and greeted Jack with a smile.

"Hey Jack! Is there anything I can do for you?" Twilight asked.

"I wanted to write a reply to Celestia about the wedding plans." Jack replied.

"Alright, I'll go get Spike." Twilight said. She walked towards the bookcases, trying to look for the purple dragon. Eventually, Twilight found Spike and asked him to write a letter. Jack explained the proposal to Spike, and within a few minutes, the dragon had sent the letter on it's way to the castle.

"Hopefully Celestia will write back soon. Is anypony else helping you with the wedding?" Twilight asked.

"Yeah, Rarity's making the clothes and Pinkie's planning the decorations." Jack replied.

"You should go and check up on them, see how they're doing." Twilight said. Jack nodded and proceeded to leave the town library. He started walking towards sugercube corner. Once there, he knocked on the door. Ms. Cake answered.

"Oh hello there Jack! Congratulations on the wedding!" She exclaimed.

"Thank you. I just came to check up on Pinkie Pie and see how she's handling." Jack said.

"Of course, she should be upstairs in her room." Ms. Cake responded. Jack walked upstairs and knocked on the door of Pinkie's room. She answered surprisingly quickly.

"Hey Jack! What are ya doing here?" Pinkie said.

"I just came to check how you were doing with the party for the wedding." Jack replied.

"Oh Jack! This is going to be the bestest party EVER! We're gonna have balloons and cupcakes and music and-" Pinkie Pie was cut off by Jack.

"That's nice to hear, is it coming along nicely?" Jack asked. Pinkie nodded.

"Yeah! We should have it ready in about two days!" Pinkie exclaimed.

_"Two whole days to make a party, Pinkie's really devoted to this stuff..." _Jack thought to himself. He walked back downstairs and eventually outside. He started walking to the Carousel Boutique. Rainbow was right, he could feel the first drop of rain on his forehead. He decided to make it more simple and just teleport to the Boutique. He knocked on the door and in a few moments, was answered by Rarity.

"Oh Jack! Hurry and come in! It's positively pouring with rain outside." Rarity exclaimed. Jack looked back outside, only a couple of drops had fallen.

"Rarity, I think you're overreacting..." Jack said. Whenever he walked into the Boutique, the small cat on the windowsill would always give him a funny look.

"So, how can I help you Jack?" Rarity asked.

"I was just wondering how the clothes for the wedding are coming along." Jack replied.

"Oh, you need not worry Jack! These garments are going to be of the finest quality I assure you!" Rarity said.

"That's good to hear. Oh, and Rarity?" Jack asked.

"Yes dear? What is it?" Rarity asked.

"Why does that cat always give me a dirty look when I come in here?" Jack asked.

"Oh, Opal is just nervous around strangers is all." Rarity said. Jack felt reassured.

"Well, I'd better head back home, Rainbow probably finished work by now." Jack said.

"Yes, I'm sure the two of you have some planning to do." Rarity said.

"Yeah..." Jack said with a nervous laugh.

"_Not really, that cat is just really starting to creep me out..." _Jack thought. He stepped outside of the Boutique. The rain was now heavy enough to start making puddles. Jack had used too much of his magic power to simply teleport there. He started running into the Everfree forest. Once inside, the rain wasn't as heavy. The growth of the trees meant that little of the rain managed to escape through. He slowed his pace and started to walk back to his house. Once he had finally reached his house. He noticed a slightly damp letter lying on his doorstep. He picked it up. It must have been a response from Celestia, considering it had the royal seal on it. He walked inside and started to read the letter.

_Dear Jack_

_I have read your most recent letter and I have approved that the wedding should be in three days. Rainbow Dash will be excused from work during this time to compensate for stress. I would like to express my deepest respect for your decision. Naturally, the wedding will be held in Canterlot. I hope that your wedding will turn out to be one of the most cherished moments in your life._

_-Princess Celestia_

__Jack smiled as he finished the letter. It probably was going to be an unforgettable moment in his life. He heard Rainbow coming from the stairs.

"Oh, you're home." Rainbow said.

"Yeah, I got a reply from the princess, she said the wedding will be held in Canterlot in three days." Jack explained.

"Sounds good to me." Rainbow said.

"Oh yeah, you're getting three days off work as well." Jack said.

"Wow really? why?" Rainbow asked.

"To compensate for stress." Jack said. He started heading upstairs. He put on his PJ's and took out his dossier.

_Entry 21_

_The wedding's gonna be held in three days, this is probably one of the most important parts of my life right now. I doubt any other human will come across either this house or this dossier, but if you do, just enjoy your time in Equestria, it's a lovely place._

_-Jack Tailor_

***Yawn* Ugh... Tired Cupzy equals late chapter. So yeah, I intend to finish this story in three more chapters. Although I'm going to be starting a new story immediately. I've got a slightly less crap idea for a romance fanfic. Credit to Redoktober for inspiring me to write this fanfic. Once again, sorry for the late chapter. Peace.  
**

**-Cupzy**


	22. Despair

Jack yawned. He slowly slipped out of bed to not wake up Rainbow. He put on some decent clothes and walked downstairs. The downpour from yesterday hadn't stopped yet and it was only getting worse. Jack started to make himself some toast.

_"Two days left until the wedding. It seems like everything's going according to plan..." _Jack thought to himself. Rarity assured him that the necessary garments would be created in time for the wedding. And Pinkie convinced Jack that the wedding party would be one to remember. In Pinkie's standards, that sounded pretty dangerous. He heard the familiar sound of hooves coming down the stairs.

"If you're going to wake up two minutes after I do. Then why not just come downstairs at the same time as me?" Jack asked. Rainbow mumbled something about "Stupid..." and sat down on the couch. Jack put the toast on a plate and sat down next to Rainbow.

"Hey! Where's my breakfast?" Rainbow asked. Jack sighed.

"Go make it yourself..." Jack said. Rainbow nodded and walked towards the kitchen. Jack realized what he had just said and leaped for the kitchen. Rainbow was looking at the toaster in a confused manner.

"So... How does this thing work?" Rainbow asked.

"On second thought, just sit down dear. I'll make your breakfast for you." Jack said with an obviously fake smile. Rainbow shrugged her shoulders and went back to the living room. Jack proceeded to make another slice of toast for Rainbow. After making the toast and putting on to another plate, he took it back to Rainbow.

"Here's your stupid breakfast." Jack said as he put the plate down on the table. Rainbow giggled and picked the plate up.

"So, have you got any plans for today?" Rainbow asked.

"Everything seems to be coming along nicely. I just have trouble coping with the fact that I'm getting married in two days..." Jack said.

"Yeah, it's pretty weird, isn't it? Out of all my friends, I thought that I would be the last one to get married." Rainbow said.

"I thought I would be back in London before this kind of stuff happened." Jack said.

"London? Where's that?" Rainbow asked.

"In my world, I lived in a place called London, a lot of people with Rarity's accent come from there." Jack explained. Rainbow nodded.

"Don't you miss your world?" Rainbow asked.

"Not really, I was about to be kicked out of my flat because of money problems. My mother was the only person who I kept in contact with and even then I didn't really talk with her that much." Jack said. Rainbow had a sad expression on her face. She never knew that Jack's past was so dark.

"Hey, my parents died when I was just a filly, at least you had a mother..." Rainbow said. She could remember the day her parents died. Or, to be more exact, murdered.

Rainbow was only a small filly, she had just been tucked inside of her bed by her mother. Her father was downstairs. After Rainbow had dozed off, she was awoken about an hour later by a scream coming from the front door. She could hear the faint noises of someone struggling and eventually, another scream was heard. Rainbow sat bolt upright in her bed. She only heard silence for the next few minutes. She heard the sound of somepony coming upstairs. If she recalled, there was two of them.

"Looks like that was everyone in the house. Grab everything valuable and let's get the hell out of here." One of the ponies said to the other, it certainly wasn't the sound of Rainbow's father or mother. She stayed completely still, lying under the covers. She was scared out of her wits. She heard the door to her bedroom open and she heard one of the ponies walking around. He must have mistaken Rainbow for a bump in the bed. Because he didn't sound like he knew she was there. He eventually sighed and walked back outside of the room. She heard the sounds of glass breaking and then there was complete silence. Rainbow quickly hurried out of her bed and downstairs.

Glass was shattered, the place had been wrecked, but the one thing that caught Rainbow's eye was the figures of two ponies lying on the ground. Her father, and her mother. She quickly hurried over to the bodies of her loved ones. She noticed that her father was still breathing. He had several stab wounds near his cutie mark. Rainbow ran around to his face and noticed his eyes were still open. Rainbow held his hoof, as if to stop him from being taken away. Her father gave a smile, happy that his daughter hadn't been hurt. After a few moments. His hoof went limp, and his eyes were closed. She quietly sobbed to herself as she lost both of her parents in an instant. Her mothers throat had been slit. She was killed instantly.

After a few hours. Some emergency paramedics came to see to her father and her mother. She was taken to the hospital where the bad news that both her father and mother had been murdered had been delivered. She was moved to an orphanage in Canterlot. When she was finally old enough to leave the orphanage, she got a job at the weather station and made enough money to afford a house. In a few years, she had met all of her friends. And the bad memories seemed to flush away whenever she was around them.

Jack was deeply moved by Rainbow's story, he thought that he had it hard. He noticed that Rainbow had shed a few tears, no wonder that the trauma had come back from those fateful days. He shifted over to her side of the couch and gave her a tight hug.

"It's alright Dashie. This is what I'm here for..." Jack said, attempting to comfort the distressed mare. She looked up at Jack and gave him a reassuring smile.

"I'll be fine, it's not the first time that I've told this story to somepony." Rainbow said in between sniffles.

"There's no need to be depressed, not when your own wedding is approaching." Jack said. Giving her a soft smile. Rainbow leaned in and felt Jack's lips meet hers. He was right, there was no reason to feel sadness when one of the happiest moments of her life was about to happen. Jack pulled away, they stared into each others eyes for a moment.

"I love you." Jack said. This made Rainbow blush a little.

"Yeah, I love you too." She replied.

"I'm going to go see Twilight. I need her to write another letter to Celestia." Jack said.

"Alright, I'll probably go into Ponyville too, I need to catch up with the girls anyway." Rainbow said. Jack nodded and snapped his fingers. He appeared outside of Twilight's library. He knocked on the door, Twilight answered.

"Hey Jack! What can I do for you?" Twilight asked.

"Hey Twi, could you get Spike to write a letter to Celestia asking exactly where in Canterlot the wedding is going to be held?" Jack asked.

"Sure! I'll get Spike right on it! Spiiiiiike!" Twilight called as Spike came out from behind a bookcase. In a few moments, he was using his magical green breath to send the letter on it's way to the castle. Jack waved goodbye to Twilight as he left the library. Rainbow's past was still in his mind. He never imagined that someone so egomanaical would have such a depressing back story. Jack was so lost in thought that he didn't see a certain pink pony jumping towards him.

"Hey sleepy head!" Pinkie shouted. Jack was startled. He gave a nervous laugh.

"Sorry Pinkie, I was just thinking about stuff." Jack explained.

"I've been looking EVERYWHERE for you! I wanted to tell you that the decorations for the party are almost done! Rainbow came along a couple of minutes ago and started helping me with the decorations! I'm probably going to get them finished by tonight!" Pinkie said, ever ecstatic.

"That's good to hear." Jack responded.

"She seemed kinda depressed though... She decided to take a nap in my room." Pinkie said, this was the quietest he had ever seen Pinkie go. He hung his head low, bringing up family matters wasn't such a good idea after all... Pinkie had already jumped away to catch a butterfly that she had her eye on for quite some time. Jack chuckled and decided to go to sugercube corner to find Rainbow. The rain had subsided a little, but was still strong enough to cause some distraction. He quickly ran over to sugercube corner. He knocked on the door and walked inside. He didn't have time for anyone to answer, his hair was soaking.

"Oh hello Jack! You look... Well, do you want me to get you a towel?" Ms. Cake asked.

"No, no. I'm fine, I just came to see Rainbow Dash." Jack said.

"Oh, she's upstairs, I think she's sleeping." Ms. Cake responded. Jack nodded and slowly made his way upstairs. He slowly pushed open the door to Pinkie's bedroom and saw Rainbow lying on the bed, fast asleep. The image was adorable. Jack smiled and sat down on the edge of the bed. This made Rainbow wake up. She lazily picked herself up from the bed and was startled when she saw Jack sitting there.

"Ah! Oh, hi Jack. You startled me there for a second, I imagined you'd be doing something else." Rainbow said.

"I decided to come over after I heard that you were pretty depressed." Jack replied.

"Yeah, I always get choked up when I talk about my family." Rainbow said.

"I'm sorry, I shouldn't have pushed you to talk about them... I never knew..." Jack said.

"It's alright, I'm just happy to have you around." Rainbow said. Giving Jack a smile.

"Likewise. We should head home, it's getting pretty late." Jack said. Rainbow nodded. She held on to Jack's trouser leg and he snapped his fingers. They reappeared outside of Jack's home, where the rain was blocked by the trees. Jack opened the door and stepped inside. His hair was still soaking wet from the rain. He walked upstairs to the bathroom and used one of his towels to dry his hair off. He walked through to his bedroom where Rainbow was already dozing off. He chuckled. He put on his PJ's and took out his dossier.

_Entry 22_

_Turns out Rainbow has a darker past than I had imagined. Her parents were murdered when she was young. Either way, it's two says until the wedding. I have to say, I'm actually looking forward to it. Celestia's going to send me a letter explaining where the wedding is going to be taking place in Canterlot. _

_-Jack Tailor._

**Sad, sad, depressing chapter. So... Yeah! These are my last three chapters. (Including this one) until I wrap this story up. I'll be making my new story pretty much immediately after I finish this one. (I'll probably make an epilogue to this story as well. I won't count it as a chapter though.) Credit to Redoktober for inspiring me to write this fanfic. (By the way, anyone got a name for my next main character? I'm going to make it a pony, so a two-word name is in order. It would be very much appreciated.) Peace.**

**-Cupzy **


	23. Jack's past

Jack sat up in his bed. The wedding was tomorrow, he gave Rainbow a nudge with his hand. He heard a few grumbles.

"Hey, Dashie, wake up. We've got a lot of stuff to do today." Jack said. Rainbow let out a large yawn and looked at Jack with a warm smile.

"Last day before the wedding. Scary, huh?" Rainbow said.

"Yeah, hopefully Celestia's replied to the letter that got sent yesterday" Jack said. He walked downstairs and opened the door. There was a letter at the doorstep. Jack picked the letter up and started to read it.

_Dear Jack_

_In response to the letter you sent me, the wedding will be held in the court garden near the castle. In preparation for this, we would be grateful if you could stay in Canterlot on the day before the wedding, this will allow us to contact you much easier. I have already sent an invitation to Twilight and her friends asking if they would also stay in Canterlot for the night. If you decide to stay in Canterlot, a luxury room has been prepared for both you and Rainbow Dash, Twilight and her friends will also stay in the same hotel. If you decide to go, you and any of your friends can take the train to Canterlot._

_-Princess Celestia_

Jack folded the letter back to it's original state.

_"A night in Canterlot, I'll talk to Dash about it when she wakes up." _Jack thought. Almost on cue, he heard the sound of Rainbow lazily walking down the stairs. She sat on the couch, still half asleep and nearly dozing off. She was like that every morning.

"Hey, Dashie. The princess wants us to stay in Canterlot tonight to make things easier, do you want to go?" Jack asked. Rainbow lazily slouched her head in Jack's general direction.

"Are any of my friends coming along?" Rainbow asked. She had a slight slur in her voice.

"She's sent invitations to all of them, so yeah, probably." Jack replied.

"Sure, if they all agree to come then I'll go." Rainbow said. Jack took it as a yes. He started to make some breakfast for him and Rainbow.

(At Twilight's house)

"Hey, Spike! We've been invited to stay with Jack and Rainbow in Canterlot tonight for the wedding, do you wanna go?" Twilight said to Spike, who was taking out a book from the shelf via a ladder.

"Uh... Yeah, sure. I don't really want to miss the wedding of one of your friends." Spike replied. Twilight smiled at him.

(At the Carousel Boutique)

"This is a positively wonderful opportunity to see what the people of Canterlot think about my designs! Oh yes... And Rainbow Dash's wedding is also very important." Rarity said to herself.

(At Fluttershy's house)

"This is wonderful! I get to see one of my best friends get married!" Fluttershy said with a smile that could melt icebergs. Her voice still quiet as a mouse, even when talking to herself.

(At Sweet Apple Acres.)

"Hey Big Macintosh! We got these here invitations ta Rainbow's weddin', Ya wanna go?" Applejack asked her brother, waving two invitations in his face. He smiled and looked at her.

"Eeyup. We can get some farmhands to mind the farm." Replied Big Macintosh.

(At Sugercube Corner)

"Omigosh! They won't be able to DESCRIBE how cool this party's gonna be!" Pinkie Pie said excitedly to herself.

(Back at Jack's house)

Jack had just prepared some cereal for them both. Yeah, he was pretty sure all of her friends would want to come along. He placed one bowl down on the table, Rainbow reluctantly picked it up.

"So we're going to have to meet up at the train station. You'll have to take me there, I have no clue where that is..." Jack said. Rainbow let out a small laugh.

"Hey Jack, can I ask you something?" Rainbow asked.

"Yeah, sure. What do you want to know?" Jack replied.

"Well, since I told you about my past, shouldn't you tell me about yours?" Rainbow said. Jack was a little less open about his past than Rainbow, but he was willing to tell her, considering she is his future wife.

"Alright, I'll give you the rundown." Jack said. Rainbow made herself comfy, something told her that this was going to be a long story.

Back on earth, Jack was bullied relentlessly simply because he didn't have anyone he could call a friend. His first days at high school was probably the best part of it, considering nobody actually knew that he had no friends. Once he had gotten his first lessons out of the way, things looked like they were looking up. While he was walking out of the history room, he bumped into somebody on the way out, knocking one of the lens out of their glasses.

"Hey, I-I'm sorry." Jack said. He noticed he was talking to a girl, he had always been nervous when talking to girls. It didn't help that the girl was pretty, too. She had long, black hair that went past her shoulders, she had a brooch pinned on the back of her hair.

"I'm sure it wasn't your fault. But could you help me look around for the lens that fell out?" The girl asked him. Jack nodded, although he wasn't sure if she'd seem him nod or not. The floor outside of the classroom was a black carpet. And it was easy to spot the lens from where Jack was standing. He picked the lens up and handed them to the girl. She smiled warmly at him.

"Thanks. Hey, do you... Like, hang around with anyone at all?" The girl asked him. Jack shook his head. He didn't know anyone at this school. He just kept to himself most of the time.

"Neither do I... I was hoping that I could just meet a group of girls and... Just fit in." The girl said. she stuck her hand out at Jack.

"My name's Celine! Nice to meet you." She said, Jack shook her hand in return.

"Uh... Yeah, my name's Jack" He replied, he could feel the red rushing to his cheeks, if he blushed now. He wouldn't hear the end of it. He managed to console himself for the time being. Celine just smiled at Jack.

"You're really quiet!" She said.

"Yeah, I don't tend to talk to anyone much." Jack replied.

"I think it's cute!" Celine said. Her sentence shook Jack from the core, that was the first time anybody, let alone a girl, gave him a compliment. Jack couldn't hold it in anymore, he felt the scarlet rushing to his cheeks. The two just remained silent for a minute. He heard the bell ringing.

"Oh! We're gonna be late for the next lesson!" Celine finally said. This gave Jack a quick chance to escape. He started walking towards his next lesson, with Celine following not far behind. After the day had finished. Everyone was either waiting outside for the bus to take them home or were just messing around on the school grounds. Apart from Jack, his house was a five minute walk from the school, so he never really had to rush home. He found a bench similar to the one he spent a lot of time sitting on back in primary school. After a large portion of the crowd were gone. He stood up and started to walk home. Just as he was about to cross the street, however. He heard a familiar voice call him from behind.

"Hey! Jack!" He could hear Celine shouting. He turned around and was greeted by a very happy looking Celine.

"Hi Celine." Jack said, still as quiet as ever.

"Do you walk home as well?" Celine asked.

"Yeah, I live just around the corner." Jack said.

"So do I! That means we can walk home together!" Celine said. She had certainly taken a shine to Jack, but he paid no heed.

_"Great, more embarrassment" _Jack thought. The two continued down the road until they came to Jack's house.

"Well, this is my house." Jack said.

"Alright. I'll see you tomorrow, okay?" Celine said, a warm smile across her face. Jack couldn't help but smile back. He walked into is house, giving Celine a wave as he opened the door. His dad was sitting in the living room when he came in.

"Got yerself a girlfriend already Jack? That was quick." His dad said. Jack did a fake laugh and went upstairs. He didn't have anything to do today. He laid down on his bed. Things were actually going well for once. If he just kept to himself, he could avoid the bullies, he was enjoying his lessons so far. And, if he played his cards right, he could end up with a girlfriend by the end of the year. Both his mother and father were out working that night. Jack went to sleep with a smile on his face, knowing that things were definitely going to go well from now on. But, instead of waking up in his hopefully going-to-be-good life, he was thrown into a world of talking ponies.

"Oh wow, so either way you probably would have gotten a marefriend?" Rainbow asked.

"As much as I would have preferred my old life, being here isn't so bad. I got some friends, I can use magic, I met you." Jack said, counting all of the things on his fingers. This made Rainbow giggle a little.

"Well, we'd better head to the train station, our friends are probably waiting for us." Rainbow said. Jack nodded and they both left the house. They started to walk to the train station. When they arrived, all of their friends were there. Even Twilight managed to bring Spike along! They all greeted the couple with a warm welcome. The train didn't take much time to arrive, but the actual trip to Canterlot took an excruciatingly long amount of time. After several hours. The group finally arrived in Canterlot. A royal guard escorted them to one of the most fancy hotels Jack had ever seen in his entire life. He and Rainbow Dash were escorted to the the large room at the top of the hotel, while the other ponies had slightly less luxurious rooms. Albeit Twilight, who had to get a room with a double bed because of Spike

Jack was tired, the journey was long, and his wedding was tomorrow. He slowly slipped into his PJ's and took out his dossier.

_Semifinal entry_

_So, we're sleeping in this fancy hotel for the night in Canterlot. The wedding will be at 3 o clock tomorrow. I still find the situation to be quite funny. I mean, a human marrying a pony. Well, the trip was long and I just really want to head to sleep._

_-Jack Tailor._

**Yup. Tomorrow is the end of Anxiety. Oh noes. Anyway, I had to take care of my still badly crippled dog today so the chapter was a bit late. Credit to Redoktober for inspiring me to write this fanfic. (And by the way, I intend for there to be an epilogue which I'm not counting as a chapter) Peace.**

**-Cupzy **


	24. True Love Is Magic

Jack opened his eyes, today was the day of his wedding. He was met with a perplexing set of emotions. But he was happy in the end. He never had a good chance to take a look around the room he fell asleep in last night. It certainly looked like nothing Jack could afford. Even the chairs looked like they cost a million bits each. Jack shook his head, there was no time to examine his surroundings, not when he had a wedding to attend! He looked at the clock... In 4 hours... He sighed, maybe he got himself too worked up last night. He brushed the sleep from his eyes. The bed felt comfier that his. He almost felt sad to get out of it. He assumed that, being one of the most expensive hotels in Equestria. It probably had a dining hall somewhere. Probably near the ground floor.

He lifted himself out of bed, he could feel the strain of his muscles adapting to the sudden movements since their peaceful rest. He put on some decent clothes as he set off for breakfast. He decided to leave Rainbow be. She needed to be as rested as possible for this. He opened the door to his bedroom. It must have been heated from the inside, as he felt a distinct chill to the air around him, it made him want to snuggle back up in the bed with Rainbow. He shook his head and started walking down the hallway. He eventually came across an overly fancy looking elevator. He stepped inside, letting an old couple slowly make their way out of the elevator before him. It was one of those useful elevators that actually had little nameplates next to them telling you where they actually led. He found the one that said "Dining room" and he pressed the button. He could hear the elevator groan to life as it shut its doors. The elevator eventually opened to a vast and empty dining hall.

He could see some of the chefs behind the counter yawning and preparing for a long days work. The dining room was almost completely empty, the only ponies he could point out were his friends sitting at multiple tables waving at him. He waved back and started to walk over to them. he dining hall was certainly meant for parties. Surely a dining hall couldn't get THIS full in a single night. He heard the voice of one of his friends as he approached them.

"Well, here's the lucky colt himself. Nice of you to show up." Twilight said jokingly, still not knowing what to say instead of colt, she still only had a small knowledge of the human world. Jack chuckled and sat down at an empty table.

"So, where's Rainbow?" Twilight asked him.

"Still sleeping." Jack responded, he still felt groggy from waking up.

"Classic Rainbow Dash, even on an event like this she still loves to sleep in." Twilight said, letting out a small laugh.

"So, Jack! How does it feel?" Asked Rarity. Jack pulled an confused expression.

"What does what feel?" Jack asked. Rarity rolled her eyes.

"How does it feel to wake up knowing that today you will be wed to the love of your life?" Rarity asked, being a little over dramatic.

"I think that "The love of my life" is pushing it a little too far, Rarity. Rainbow would never let me hear the end of it if I called her that, I'd probably get a black eye too." Jack replied. This got a small laugh out of everpony. Even Fluttershy made a small attempt at laughing.

"Anyway, back to my question. How does it feel to know that tomorrow, you could be taking Rainbow Dash on a romantic dinner? I can just imagine the candles flickering as you both move in closer to each other for a kiss that will-" Rarity finished her sentence as she was cut off by Twilight.

"You're going a bit far Rarity." Twilight said, Rarity suddenly had a blush across her face. She had never meant to go into that much detail.

"I do apologize Jack, my heart simply skips a beat when I hear the romantic stories of another lucky, er... Man, was it?" Rarity asked, her knowledge of the human world also restricted. Jack nodded at her.

"It's alright Rarity, although a romantic dinner is something Dashie would never agree to go on." Jack replied.

"I bet she forgets that she's actually married when she wakes up tomorrow!" Pinkie said. She seemed more excited that the others for the wedding.

"Oh, and since you didn't wake up Rainbow, you're not supposed to see her before the wedding." Twilight said.

"What? Why's that?" Jack asked.

"It's bad luck to see the bride before the wedding, dear" Rarity said. Jack nodded. He was still wondering if staying in the bed was a good idea.

"Anyway, back to the plan for the wedding. It's going to take place in the royal garden, the one where Discord's statue is. There's probably going to be a large crowd, considering this is a marriage between the strongest being in Equestria and one of the elements of harmony. Rarity will give you both your clothing before the wedding starts, you can both get changed in your own rooms, because this place is pretty close to the gardens. Pinkie will set up the decorations beforehand. Is that alright with everyone?" Twilight said. She sounded like a business executive. Everyone nodded and left their seats.

Jack had four hours to waste, one was wasted in the hotel so he only had to wait three hours. He decided to take a walk around Canterlot, he had never actually got to admire the city, he had only been here once for the Canterlot festival but he had his mind focused on other things than pretty scenery when he was there. If the houses weren't that small, it would bear a striking resemblance to the more busier parts of London. Ponies of all sizes were wandering the streets either heading to work or getting their children to run errands for them. Children, that was a word that worried Jack. Would Rainbow ever agree to children? He threw the thought to the back of his mind. It was simply too early in the morning to be thinking that.

He had wasted another hour wandering through the city. Some of the ponies recognized him and gave him smiles and "Congratulations" while he was walking through Canterlot. He could see several farmers pulling a cart of supplies through the city. It appeared that this was quite a busy day for Canterlot. He started heading back to the hotel. It was now one o clock. He imagined that Twilight wanted them to meet back around 2 o clock, being the perfectionist she is, she probably wants the wedding to fall into place before it had even started.

He decided to go and look at the royal garden, he had been there before but he only looked at it for a few moments. Jack walked in the direction that he thought the garden was in. Sure enough, he eventually came to a large expanse with cobblestone paths and statues dotted around the area. Pinkie had already set up the decorations. There were small white tables and chairs around a stone pathway, there was also a small podium meant for the priest. There were small cupcakes that looked too carefully-made to be made by Pinkie Pie. There were decorations that were clearly made to entertain small colts or fillies that somepony might have brought along. The long walk had made another hour go by. He decided to start walking back to the hotel. Twilight and her friends were probably all waiting for him.

He continued to walk back to the hotel, he could hear some ponies telling each other about the wedding. When Jack had finally reached the hotel, he went back to the dining hall. All of his friends were waiting for him near the back. He walked up to them and sat down on a chair opposite Twilight.

"It's good to see you again Jack." Twilight said. Jack took a quick look around the tables.

"Where's Rainbow?" Jack asked.

"She's getting changed in my room. You should probably go get changed too. Rarity left the suit on your bed." Twilight explained. Jack nodded and proceeded back to the elevator. Rainbow in a wedding dress, he wondered what it would look like. Rarity usually based all of her designs off the personality of the wearer. Although a Rainbow colored wedding dress would be a bit of a mood killer. He shrugged, he would see in due time. He made his way back to the room. He saw a tuxedo folded on the bed. It looked to be Jack's exact size, even though Rarity never did any real measurements on him. He put the tuxedo on. It was actually pretty comfortable. He smiled to himself and took the elevator back downstairs. All of his friends made a "oooooh"noise as Jack walked back towards them. Rarity just blushed, happy at her own work.

"Well, it looks like everything's ready!" Twilight said enthusiastically. Jack looked at his wrist watch. The time had just hit 3 o clock. He looked out of a window that was facing the garden. Some patrons had already turned up and were sitting on the many chairs and tables.

"Alright girls, you can go. I'll have a talk with Jack." Twilight said. All of the other ponies nodded and started walking towards the garden. Twilight looked at Jack.

"Alright, in a few moments, I'll tell you when to go out. I'll give you a signal. Follow me." Twilight said, she led them to an area just outside of the garden where no one could see them. After everyone had settled down. Twilight gave him a little "Go now" hoof movement. He walked slowly and in his most formal walk cycle towards the podium. After he had finally reached the end. All of the ponies attention was focused on him. Some were whispering, some just stayed silent. After a few moments which felt like hours. Some of the ponies near the back drew their own attention towards a figure walking towards them. It took Jack a few seconds to register the pony. When he had identified the pony as Rainbow Dash he smiled, he finally got a good look at her dress. In certain spots, the dress was colored in a rainbow-like fashion. The rest of the dress was an incredibly light cyan. Rarity had certainly outdone herself.

Rainbow had the biggest smile that Jack had ever seen on her before. She started to walk towards the podium. The long dress waving behind her as she did so. When she had reached the podium. She looked at Jack and gave him a heart warming smile which Jack returned. They both turned their attention to the priest standing at the podium. They both remained silent as the priest gave his speech.

"We are gathered here today to celebrate the gift of marriage to these two Equestrian citizens." The priest continued on with his speech until he got to the main part.

"Do you, Rainbow Dash. Take this man to be your lawfully wedded husband, 'till death do you part?" The priest asked Rainbow. She had a smile on throughout the entire speech.

"I do." Rainbow replied, which was the most polite thing she had ever said.

"And do you, Jack Tailor. Take this mare to be your lawfully wedded wife, 'till death do you part?" The priest asked Jack.

"I do." Jack replied.

"Then, by the power invested in me by princess Celestia, I now pronounce you man and mare. You may kiss the bride." The priest declared. Jack felt a little embarrassed having to kneel down to be able to kiss Rainbow, but it was certainly worth it. Jack felt Rainbow's lips press against his own. This was certainly the longest kiss they had ever had. After about thirty seconds, Rainbow pulled away. The entire crowd was cheering after they had finished. Every one of his friends had either broken into tears or was currently shedding one. Even Pinkie's eyes were full of tears. After a few moments of cheering, the priest had dismissed everyone.

Pinkie was already on the case. She had started up some classical dance music from some unknown source. The wedding seemed to have made some ponies realize their feelings for their significant others, some ponies in the dance were kissing, others were simply dancing, and the children just played a few feet away from the crowd. Rainbow extended a hoof out to Jack.

"Isn't this the part where you ask me to dance?" Rainbow said jokingly.

"That depends on how long you can stay on two hooves." Replied Jack. Rainbow giggled and let Jack help her to her standing position. Soon enough, the two of them were now the main focus of everyone, many ponies had stopped dancing to watch them. Rainbow was a surprisingly good dancer which took Jack by surprise at first. But he managed to get the hang of it. The night went in quickly and everpony but Jack and Rainbow had their fair share of alcohol. Most were starting to go home exclaiming at how much fun they had. Jack and Rainbow smiled when they saw their friends walking up to them.

"Congratulations you two!" Twilight exclaimed.

"Yes, I would go into another long winded discussion about love and passion but I believe that you two have already exceeded my expectations." Rarity said.

"That was one of the best parties EVER!" Pinkie shouted.

"Ah'm really happy for you both!" Applejack said.

"Yes, I hope you two are really happy together." Fluttershy said, much louder than Jack had anticipated. Both Rainbow and Jack looked into each others eyes. They smiled warmly at each other. After a few more minutes had passed, all of them started to take the train back to Ponyville. They were all happy and, in Rarity's case, somewhat jealous of Jack and Rainbow. When the group finally arrived in Ponyville, the mayor ha arrived to give a congratulations to both Jack and Rainbow. Everpony started to go their separate ways. And Jack and Rainbow started walking back to their house. They hardly said a word to each other as they walked home. Jack was surprised when he looked at his wrist watch and realized it was almost one o clock in the morning. They both had to go to sleep.

When he finally entered the house with Rainbow, he noticed how tired he was. He began to walk upstairs. Shortly followed by Rainbow Dash. Jack slipped on his PJ's and took out his dossier.

_My final entry_

Me and Rainbow got married today and I honestly couldn't be happier, it turned out perfectly. We haven't said much to each other since but I think the silence is enough to tell each other that we're happy to be together. If another human finds this journal. Then it doesn't matter how happy you were on earth. You'll be even happier in Equestria.

-Jack Tailor

Jack yawned and put his dossier on his bedside cabinet. Rainbow crawled into bed and they both just smiled at each other for a while. After a few minutes, they both whispered in unison:

"I love you."

**So yeah... That was the end of Anxiety. (Epilogue's coming tomorrow along with he first chapter of my new story.) So yeah, that was my first fanfic EVAH. And I have to say that it was incredible fun to write. I thank all of my viewers and all the people who took time out of their day to write me a review. A huge thanks to Redoktober for inspiring me with his fanfic "Insomnia" Peace.**

**-Cupzy**


	25. Epilogue - Life's Just Beginning

Jack awoke and yawned, he looked over at the wristwatch he left on the table. 9 o clock!? He was going to be late! He put on some clothes and opened the door to his bedroom, he was greeted by a small, overexcited filly. It was the second anniversary of Jack and Rainbow's marriage. Two entire years had passed ever since he found himself in Ponyville. During the first year, Rainbow had developed a small lump in her stomach. All of his friends were surprised to hear that she was pregnant. A few months later, Jack had a filly that he could call his daughter. After a heated argument, Jack had to finally give in and let the filly's name start with the name "Rainbow" eventually, Dash set on the name "Rainbow Swift" as she wanted it to be reminiscent of her name. By the time Swift could talk, she had already developed Dash's ego. Today was Swift's first day at school, hence the reason she was so excited.

"C'mon Dad! I wanna go to school!" Swift said. Jack chuckled at the small filly.

"Believe me, that's the last time you'll ever say that." Jack said. Swift ran downstairs. Probably to tell Rainbow that he was awake. Rainbow retained her personality even after she had a kid. That doesn't mean she didn't pay attention to the kid. When she was born, Swift was instantly put at the top of her list of her favorite pastimes. She spent most of the day around Swift, always playing games with her. She had officially (Well, not completely) given up on joining the Wonderbolts once Swift was born. Jack walked downstairs and saw Dash hugging Swift.

"Try to stick in at school, alright? Don't do what I did and drop out early on!" Dash said. Swift nodded and looked at Jack. Dash figured that Jack was more suited to taking Swift to school Considering that there are creatures in the forest that Jack could stand up to. Swift adopted her mother's rainbow colored hair, but her body was instead Jack's skin color. She preferred to wear her hair in a ponytail rather than not tending to it at all. Rainbow gave Jack a morning kiss and warned him not to let anything happen to Swift, or else she would kill him. Jack nodded. He and Swift stepped outside. It was a sunny day. Swift was ecstatic about her first day at school.

The two continued down the path that Jack had walked down countless amounts of times. Once they had finally reached Ponyville. They started walking towards the school. A lot of other stuff had happened over the years. None of his friends were married yet, all but Rarity had a coltfriend however. Poor mare, her tastes were a little too refined for Ponyville. Once they had reached the school. Jack knelt down and looked Swift in the eye.

"Have a great first day at school! Make lots of friends and tell me and Dash all about it when we come home! I'll be back at three o clock to pick you up, alright?" Jack said. Swift gave an enthusiastic nod and hurried towards the school. Jack couldn't help but smile when she almost tripped over from running so fast. She still hadn't learnt how to use her wings yet. Jack turned around and started to walk home. His life in Equestria was great, and with Swift in his life, it was only going to get better.

_The end_

**Alright, a very short ****epilogue. It took me like ten minutes to finish. If the ending seems rather abrupt then I'm sorry, I ran out of ideas. I decided to upload this today because I was bored and I was just like "Ah, Fuck it, I'ma write me some epilogues." and then I made an epilogue. Credit to Redoktober for inspiring me to write this fanfic. Peace.**

**-Cupzy**


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